Tricyclic benzoylpyrazole derivatives

ABSTRACT

Tricyclic benzoylpyrazole derivatives of the formula I  
                 
where: 
     X is oxygen, sulfur, S═O, S(═O) 2 , CR 6 R 7 , NR 8  or a bond; Y together with the two carbons to which it is attached forms a saturated, partially saturated or unsaturated 5- or 6-membered heterocycle;    R 1 , R 2 , R 6 , R 7  are hydrogen, alkyl, haloalkyl, alkoxy or haloalkoxy;    R 3  is halogen, alkyl, haloalkyl, alkoxy or haloalkoxy;    R 4  is hydrogen, nitro, halogen, cyano, alkyl, haloalkyl, alkoxy, haloalkoxy, alkylthio, haloalkylthio, alkylsulfinyl, haloalkylsulfinyl, alkylsulfonyl, haloalkylsulfonyl, unsubstituted or substituted aminosulfonyl or unsubstituted or substituted sulfonylamino;    R 5  is hydrogen, alkyl or halogen; l is 0, 1 or 2;    R 8  is hydrogen, alkyl, haloalkyl, alkylcarbonyl, formyl, alkoxycarbonyl, haloalkoxycarbonyl, alkylsulfonyl or haloalkylsulfonyl;    R 9  is substituted pyrazol-4-ylcarbonyl or substituted 5-oxopyrazolin-4-ylmethylidene; and their agriculturally useful salts; processes and intermediates for preparing the tricyclic benzoylpyrazole derivatives; compositions comprising them and the use of these derivatives or of the compositions comprising them for controlling undesirable plants are described.

The present invention relates to novel tricyclic benzoylpyrazole derivatives of the formula I

where:

-   -   X is oxygen, sulfur, S═O, S(═O)₂, CR⁶R⁷, NR⁸ or a bond;     -   Y together with the two carbons to which it is attached forms a         saturated, partially saturated or unsaturated 5- or 6-membered         heterocycle which contains one to three identical or different         heteroatoms selected from the following group: oxygen, sulfur or         nitrogen;     -   R¹, R², R⁶, R⁷ are hydrogen, C₁-C₆-alkyl, C₁-C₆-haloalkyl,         C₁-C₆-alkoxy or C₁-C₆-haloalkoxy;     -   R³ is halogen, C₁-C₆-alkyl, C₁-C₆-haloalkyl, C₁-C₆-alkoxy or         C₁-C₆-haloalkoxy;     -   R⁴ is hydrogen, nitro, halogen, cyano, C₁-C₆-alkyl,         C₁-C₆-haloalkyl, C₁-C₆-alkoxy, C₁-C₆-haloalkoxy,         C₁-C₆-alkylthio, C₁-C₆-haloalkylthio, C₁-C₆-alkylsulfinyl,         C₁-C₆-haloalkylsulfinyl, C₁-C₆-alkylsulfonyl,         C₁-C₆-haloalkylsulfonyl, aminosulfonyl,         N—(C₁-C₆-alkyl)aminosulfonyl, N,N-di(C₁-C₆-alkyl)aminosulfonyl,         N—(C₁-C₆-alkylsulfonyl) amino, N—(C₁-C₆-haloalkylsulfonyl)amino,         N—(C₁-C₆-alkyl)-N—(C₁-C₆-alkylsulfonyl)amino or         N—(C₁-C₆-alkyl)-N—(C₁-C₆-haloalkylsulfonyl)amino;     -   R⁵ is hydrogen, C₁-C₆-alkyl or halogen;     -   R⁸ is hydrogen, C₁-C₆-alkyl, C₁-C₆-haloalkyl,         C₁-C₆-alkylcarbonyl, formyl, C₁-C₆-alkoxycarbonyl,         C₁-C₆-haloalkoxycarbonyl, C₁-C₆-alkylsulfonyl or         C₁-C₆-haloalkylsulfonyl;     -   l is 0, 1 or 2;     -   R⁹ is a radical IIa or IIb         where     -   R¹⁰ is hydroxyl, mercapto, halogen, OR¹³, SR¹³, SO₂R¹⁴, NR¹⁵R¹⁶         or N-bonded heterocyclyl, where the heterocyclyl radical may be         partially or fully halogenated and/or may carry one to three of         the following radicals:         -   nitro, cyano, C₁-C₄-alkyl, C₁-C₄-haloalkyl, C₁-C₄-alkoxy or             C₁-C₄-haloalkoxy;     -   R¹¹ is hydrogen, C₁-C₆-alkyl, C₁-C₆-haloalkyl, C₃-C₆-cycloalkyl,         hydroxyl, C₁-C₆-alkoxy or C₁-C₆-haloalkoxy;     -   R¹² is hydrogen, halogen, C₁-C₆-alkyl, C₁-C₆-haloalkyl,         hydroxyl, C₁-C₆-alkoxy, C₁-C₆-haloalkoxy, C₁-C₆-alkylthio or         C₁-C₆-haloalkylthio;     -   R¹³ is C₁-C₆-alkyl, C₃-C₆-alkenyl, C₃-C₆-haloalkenyl,         C₃-C₆-alkynyl, C₃-C₆-haloalkynyl, C₃-C₆-cycloalkyl,         C₁-C₂₀-alkylcarbonyl, C₂-C₂₀-alkenylcarbonyl,         C₂-C₆-alkynylcarbonyl, C₃-C₆-cycloalkylcarbonyl,         C₁-C₆-alkoxycarbonyl, C₃-C₆-alkenyloxycarbonyl,         C₃-C₆-alkynyloxycarbonyl, C₁-C₆-alkylthiocarbonyl,         C₁-C₆-alkylaminocarbonyl, C₃-C₆-alkenylaminocarbonyl,         C₃-C₆-alkynylaminocarbonyl, N,N-di(C₁-C₆-alkyl)aminocarbonyl,         N—(C₃-C₆-alkenyl)-N—(C₁-C₆-alkyl) aminocarbonyl,         N—(C₃-C₆-alkynyl)-N—(C₁-C₆-alkyl)aminocarbonyl,         N—(C₁-C₆-alkoxy)-N—(C₁-C₆-alkyl)aminocarbonyl,         N—(C₃-C₆-alkenyl)-N—(C₁-C₆-alkoxy)aminocarbonyl,         N—(C₃-C₆-alkynyl)-N—(C₁-C₆-alkoxy)aminocarbonyl,         di(C₁-C₆-alkyl)aminothiocarbonyl,         C₁-C₆-alkylcarbonyl-C₁-C₆-alkyl, C₁-C₆-alkoxyimino-C₁-C₆-alkyl,         N—(C₁-C₆-alkylamino)imino-C₁-C₆-alkyl or         N,N-di(C₁-C₆-alkylamino)imino-C₁-C₆-alkyl, where the         abovementioned alkyl, cycloalkyl and alkoxy radicals may be         partially or fully halogenated and/or may carry one to three of         the following groups:         -   cyano, C₁-C₄-alkoxy, C₁-C₄-alkylthio, di(C₁-C₄-alkyl)amino,             C₁-C₄-alkylcarbonyl, C₁-C₄-alkoxycarbonyl,             C₁-C₄-alkoxy-C₁-C₄-alkoxycarbonyl,             di(C₁-C₄-alkyl)amino-C₁-C₄-alkoxycarbonyl, hydroxycarbonyl,             C₁-C₄-alkylaminocarbonyl, di(C₁-C₄-alkyl)aminocarbonyl,             aminocarbonyl, C₁-C₄-alkylcarbonyloxy or C₃-C₆-cycloalkyl;         -   is phenyl, heterocyclyl, phenyl-C₁-C₆-alkyl,             heterocyclyl-C₁-C₆-alkyl, phenylcarbonyl-C₁-C₆-alkyl,             heterocyclylcarbonyl-C₁-C₆-alkyl, phenylcarbonyl,             heterocyclylcarbonyl, phenoxycarbonyl,             phenyloxythiocarbonyl, heterocyclyloxycarbonyl,             heterocyclyloxythiocarbonyl, phenylaminocarbonyl,             N—(C₁-C₆-alkyl)-N-(phenyl)aminocarbonyl,             heterocyclylaminocarbonyl,             N—(C₁-C₆-alkyl)-N-(heterocyclyl)aminocarbonyl,             phenyl-C₂-C₆-alkenylcarbonyl or             heterocyclyl-C₂-C₆-alkenylcarbonyl, where the phenyl and the             heterocyclyl radical of the 18 lastmentioned substitutents             may be partially or fully halogenated and/or may carry one             to three of the following radicals:         -   nitro, cyano, C₁-C₄-alkyl, C₁-C₄-haloalkyl, C₁-C₄-alkoxy,             C₁-C₄-haloalkoxy, heterocyclyl or N-bonded heterocyclyl,             where the two lastmentioned substitutents for their part may             be partially or fully halogenated and/or may carry one to             three of the following radicals:         -   nitro, cyano, C₁-C₄-alkyl, C₁-C₄-haloalkyl, C₁-C₄-alkoxy or             C₁-C₄-haloalkoxy;     -   R¹⁴ is C₁-C₆-alkyl, C₃-C₆-alkenyl, C₃-C₆-haloalkenyl,         C₃-C₆-alkynyl, C₃-C₆-haloalkynyl, C₃-C₆-cycloalkyl,         C₁-C₆-alkoxy, di(C₁-C₆-alkyl)amino or di(C₁-C₆-haloalkyl)amino,         where the above-mentioned alkyl, cycloalkyl and alkoxy radicals         may be partially or fully halogenated and/or may carry one to         three of the following groups:         -   cyano, C₁-C₄-alkoxy, C₁-C₄-alkylthio, di(C₁-C₄-alkyl)amino,             C₁-C₄-alkylcarbonyl, C₁-C₄-alkoxycarbonyl,             C₁-C₄-alkoxy-C₁-C₄-alkoxycarbonyl,             di(C₁-C₄-alkyl)amino-C₁-C₄-alkoxycarbonyl, hydroxycarbonyl,             C₁-C₄-alkylaminocarbonyl, di(C₁-C₄-alkyl)aminocarbonyl,             aminocarbonyl, C₁-C₄-alkylcarbonyloxy or C₃-C₆-cycloalkyl;         -   is phenyl, heterocyclyl, phenyl-C₁-C₆-alkyl,             heterocyclyl-C₁-C₆-alkyl, phenoxy, heterocyclyloxy, where             the phenyl and the heterocyclyl radical of the lastmentioned             substitutents may be partially or fully halogenated and/or             may carry one to three of the following radicals:         -   nitro, cyano, C₁-C₄-alkyl, C₁-C₄-haloalkyl, C₁-C₄-alkoxy or             C₁-C₄-haloalkoxy;     -   R¹⁵ is C₁-C₆-alkyl, C₃-C₆-alkenyl, C₃-C₆-haloalkenyl,         C₃-C₆-alkynyl, C₃-C₆-haloalkynyl, C₃-C₆-cycloalkyl,         C₁-C₆-alkoxy, C₃-C₆-alkenyloxy, C₃-C₆-alkynyloxy,         di(C₁-C₆-alkyl)amino or C₁-C₆-alkylcarbonylamino, where the         abovementioned alkyl, cycloalkyl and alkoxy radicals may be         partially or fully halogenated and/or may carry one to three         radicals of the following group:         -   cyano, C₁-C₄-alkoxy, C₁-C₄-alkylthio, di(C₁-C₄-alkyl)amino,             C₁-C₄-alkylcarbonyl, C₁-C₄-alkoxycarbonyl,             C₁-C₄-alkoxy-C₁-C₄-alkoxycarbonyl,             di(C₁-C₄-alkyl)amino-C₁-C₄-alkoxycarbonyl, hydroxycarbonyl,             C₁-C₄-alkylaminocarbonyl, di(C₁-C₄-alkyl)aminocarbonyl,             aminocarbonyl, C₁-C₄-alkylcarbonyloxy or C₃-C₆-cycloalkyl;         -   is phenyl, heterocyclyl, phenyl-C₁-C₆-alkyl or             heterocyclyl-C₁-C₆-alkyl, where the phenyl or heterocyclyl             radical of the four lastmentioned substitutents may be             partially or fully halogenated and/or may carry one to three             of the following radicals:         -   nitro, cyano, C₁-C₄-alkyl, C₁-C₄-haloalkyl, C₁-C₄-alkoxy or             C₁-C₄-haloalkoxy;     -   R¹⁶ is C₁-C₆-alkyl, C₃-C₆-alkenyl, C₃-C₆-alkynyl or         C₁-C₆-alkylcarbonyl;         and their agriculturally useful salts.

Moreover, the invention relates to processes and intermediates for preparing compounds of the formula I, to compositions comprising them, and to the use of these derivatives or of the compositions comprising them for controlling harmful plants.

WO 97/19087 and EP-A 860 441 disclose tricyclic compounds which are characterized in that the respective benzoyl unit that they contain is fused via positions 3 and 4 with a bicycle. However, the herbicidal properties of the prior-art compounds and their compatibility with crop plants are not entirely satisfactory. It is an object of the present invention to provide novel, biologically, in particular herbicidally, active compounds having improved properties.

We have found that this object is achieved by the tricyclic benzoylpyrazole derivatives of the formula I and their herbicidal action.

Furthermore, we have found processes and intermediates for synthesizing the compounds of the formula I. Likewise, we have found herbicidal compositions which comprise the compounds I and have very good herbicidal action. Moreover, we have found processes for preparing these compositions and methods for controlling undesirable vegetation using the compounds I.

Depending on the substitution pattern, the compounds of the formula I can contain one or more chiral centers, in which case they are present as enantiomers or diastereomer mixtures. The invention provides both the pure enantiomers or diastereomers and their mixtures.

The compounds of the formula I can also be present in the form of their agriculturally useful salts, the type of salt generally being immaterial. Generally suitable are the salts of those cations or the acid addition salts of those acids whose cations and anions, respectively, do not negatively affect the herbicidal action of the compounds I.

Suitable cations are, in particular, ions of the alkali metals, preferably lithium, sodium and potassium, of the alkaline earth metals, preferably calcium and magnesium, and of the transition metals, preferably manganese, copper, zinc and iron, and also ammonium, where, if desired, one to four hydrogen atoms may be replaced by C₁-C₄-alkyl, hydroxy-C₁-C₄-alkyl, C₁-C₄-alkoxy-C₁-C₄-alkyl, hydroxy-C₁-C₄-alkoxy-C₁-C₄-alkyl, phenyl or benzyl, preferably ammonium, dimethylammonium, diisopropylammonium, tetramethylammonium, tetrabutylammonium, 2-(2-hydroxyeth-1-oxy)eth-1-ylammonium, di(2-hydroxyeth-1-yl)ammonium, trimethylbenzylammonium, furthermore phosphonium ions, sulfonium ions, preferably tri(C₁-C₄-alkyl)sulfonium, and sulfoxonium ions, preferably tri(C₁-C₄-alkyl)sulfoxonium.

Anions of useful acid addition salts are primarily chloride, bromide, fluoride, hydrogen sulfate, sulfate, dihydrogen phosphate, hydrogen phosphate, nitrate, hydrogen carbonate, carbonate, hexafluorosilicate, hexafluorophosphate, benzoate and the anions of C₁-C₄-alkanoic acids, preferably formate, acetate, propionate and butyrate.

In the case of R¹⁰=hydroxyl or mercapto, IIa also represents the tautomeric forms IIa′ and IIa″

Likewise, in the case of R¹⁰=hydroxyl or mercapto, IIb also represents the tautomeric forms IIb′ and IIb″

The organic molecular moieties mentioned for the substitutents R¹-R¹⁷ or as radicals on phenyl and heterocyclyl radicals are collective terms for individual enumerations of the individual group members. All hydrocarbon chains, i.e. all alkyl, haloalkyl, hydroxyalkyl, alkoxy, haloalkoxy, alkylthio, haloalkylthio, alkylsulfinyl, haloalkylsulfinyl, alkylsulfonyl, haloalkylsulfonyl, N-alkylaminosulfonyl, N,N-dialkylaminosulfonyl, N-alkylamino, N,N-dialkylamino, N-haloalkylamino, N,N-dihaloalkylamino, N-alkylsulfonylamino, N-haloalkylsulfonylamino, N-alkyl-N-alkylsulfonylamino, N-alkyl-N-haloalkylsulfonylamino, alkylcarbonyl, alkoxycarbonyl, haloalkoxycarbonyl, alkylthiocarbonyl, alkylcarbonyloxy, alkylaminocarbonyl, dialkylaminocarbonyl, dialkylaminothiocarbonyl, alkoxyalkyl, hydroxyalkoxyalkyl, alkylcarbonylalkyl, alkoxyiminoalkyl, N-(alkylamino)iminoalkyl, N-(dialkylamino)iminoalkyl, phenylalkenylcarbonyl, heterocyclylalkenylcarbonyl, N-alkoxy-N-alkylaminocarbonyl, N-alkyl-N-phenylaminocarbonyl, N-alkyl-N-heterocyclylaminocarbonyl, phenylalkyl, heterocyclylalkyl, phenylcarbonylalkyl, heterocyclylcarbonylalkyl, dialkylaminoalkoxycarbonyl, alkoxyalkoxycarbonyl, alkenylcarbonyl, alkenyloxycarbonyl, alkenylaminocarbonyl, N-alkenyl-N-alkylaminocarbonyl, N-alkenyl-N-alkoxyaminocarbonyl, alkynylcarbonyl, alkynyloxycarbonyl, alkynylaminocarbonyl, N-alkynyl-N-alkylaminocarbonyl, N-alkynyl-N-alkoxyaminocarbonyl, alkenyl, alkynyl, haloalkenyl, haloalkynyl, alkenyloxy and alkynyloxy moieties, may be straight-chain or branched. Unless indicated otherwise, halogenated substitutents preferably carry one to five identical or different halogen atoms. The term halogen denotes in each case fluorine, chlorine, bromine or iodine.

Examples of other meanings are:

-   -   C₁-C₄-alkyl and the alkyl moieties of hydroxy-C₁-C₄-alkyl: for         example methyl, ethyl, propyl, 1-methylethyl, butyl,         1-methylpropyl, 2-methylpropyl or 1,1-dimethylethyl;     -   C₁-C₆-alkyl, and the alkyl moieties of         C₁-C₆-alkylcarbonyl-C₁-C₆-alkyl, C₁-C₆-alkoxyimino-C₁-C₆-alkyl,         N—(C₁-C₆-alkylamino)imino-C₁-C₆-alkyl,         N-(di-C₁-C₆-alkylamino)imino-C₁-C₆-alkyl,         N—(C₁-C₆-alkoxy)-N—(C₁-C₆-alkyl)aminocarbonyl,         N—(C₃-C₆-alkenyl)-N—(C₁-C₆-alkyl)aminocarbonyl,         N—(C₃-C₆-alkynyl)-N—(C₁-C₆-alkyl)aminocarbonyl,         N—(C₁-C₆-alkyl)-N-phenylaminocarbonyl,         N—(C₁-C₆-alkyl)-N-heterocyclylaminocarbonyl, phenyl-C₁-C₆-alkyl,         N—(C₁-C₆-alkyl)-N—(C₁-C₆-alkylsulfonyl) amino,         N—(C₁-C₆-alkyl)-N—(C₁-C₆-haloalkylsulfonyl)amino,         heterocyclyl-C₁-C₆-alkyl, phenylcarbonyl-C₁-C₆-alkyl,         heterocyclylcarbonyl-C₁-C₆-alkyl: C₁-C₄-alkyl as mentioned         above, and also, for example, pentyl, 1-methylbutyl,         2-methylbutyl, 3-methylbutyl, 2,2-dimethylpropyl, 1-ethylpropyl,         hexyl, 1,1-dimethylpropyl, 1,2-dimethylpropyl, 1-methylpentyl,         2-methylpentyl, 3-methylpentyl, 4-methylpentyl,         1,1-dimethylbutyl, 1,2-dimethylbutyl, 1,3-dimethylbutyl,         2,2-dimethylbutyl, 2,3-dimethylbutyl, 3,3-dimethylbutyl,         1-ethylbutyl, 2-ethylbutyl, 1,1,2-trimethylpropyl,         1-ethyl-1-methylpropyl or 1-ethyl-3-methylpropyl;     -   C₁-C₄-haloalkyl: a C₁-C₄-alkyl radical as mentioned above which         is partially or fully substituted by fluorine, chlorine, bromine         and/or iodine, i.e., for example, chloromethyl, dichloromethyl,         trichloromethyl, fluoromethyl, difluoromethyl, trifluoromethyl,         chlorofluoromethyl, dichlorofluoromethyl, chlorodifluoromethyl,         2-fluoroethyl, 2-chloroethyl, 2-bromoethyl, 2-iodoethyl,         2,2-difluoroethyl, 2,2,2-trifluoroethyl, 2-chloro-2-fluoroethyl,         2-chloro-2,2-difluoroethyl, 2,2-dichloro-2-fluoroethyl,         2,2,2-trichloroethyl, pentafluoroethyl, 2-fluoropropyl,         3-fluoropropyl, 2,2-difluoropropyl, 2,3-difluoropropyl,         2-chloropropyl, 3-chloropropyl, 2,3-dichloropropyl,         2-bromopropyl, 3-bromopropyl, 3,3,3-trifluoropropyl,         3,3,3-trichloropropyl, 2,2,3,3,3-pentafluoropropyl,         heptafluoropropyl, 1-(fluoromethyl)-2-fluoroethyl,         1-(chloromethyl)-2-chloroethyl, 1-(bromomethyl)-2-bromoethyl,         4-fluorobutyl, 4-chlorobutyl, 4-bromobutyl or nonafluorobutyl;     -   C₁-C₆-haloalkyl, and the haloalkyl moieties of         N—C₁-C₆-haloalkylamino and N,N-(di-C₁-C₆-haloalkyl)amino:         C₁-C₄-haloalkyl as mentioned above, and also, for example,         5-fluoropentyl, 5-chloropentyl, 5-bromopentyl, 5-iodopentyl,         undecafluoropentyl, 6-fluorohexyl, 6-chlorohexyl, 6-bromohexyl,         6-iodohexyl or dodecafluorohexyl;     -   C₁-C₄-alkoxy: for example methoxy, ethoxy, propoxy,         1-methylethoxy, butoxy, 1-methylpropoxy, 2-methylpropoxy or         1,1-dimethylethoxy;     -   C₁-C₆-alkoxy, and the alkoxy moieties of         C₁-C₆-alkoxyimino-C₁-C₆-alkyl,         N—(C₁-C₆-alkoxy)-N—(C₁-C₆-alkyl)aminocarbonyl,         N—(C₃-C₆-alkenyl)-N—(C₁-C₆-alkoxy)aminocarbonyl and         N—(C₃-C₆-alkynyl)-N—(C₁-C₆-alkoxy)aminocarbonyl: C₁-C₄-alkoxy as         mentioned above, and also, for example, pentoxy, 1-methylbutoxy,         2-methylbutoxy, 3-methylbutoxy, 1,1-dimethylpropoxy,         1,2-dimethylpropoxy, 2,2-dimethylpropoxy, 1-ethylpropoxy,         hexoxy, 1-methylpentoxy, 2-methylpentoxy, 3-methylpentoxy,         4-methylpentoxy, 1,1-dimethylbutoxy, 1,2-dimethylbutoxy,         1,3-dimethylbutoxy, 2,2-dimethylbutoxy, 2,3-dimethylbutoxy,         3,3-dimethylbutoxy, 1-ethylbutoxy, 2-ethylbutoxy,         1,1,2-trimethylpropoxy, 1,2,2-trimethylpropoxy,         1-ethyl-1-methylpropoxy or 1-ethyl-2-methylpropoxy;     -   C₁-C₄-haloalkoxy: a C₁-C₄-alkoxy radical as mentioned above         which is partially or fully substituted by fluorine, chlorine,         bromine and/or iodine, i.e., for example, fluoromethoxy,         difluoromethoxy, trifluoromethoxy, chlorodifluoromethoxy,         bromodifluoromethoxy, 2-fluoroethoxy, 2-chloroethoxy,         2-bromoethoxy, 2-iodoethoxy, 2,2-difluoroethoxy,         2,2,2-trifluoroethoxy, 2-chloro-2-fluoroethoxy,         2-chloro-2,2-difluoroethoxy, 2,2-dichloro-2-fluoroethoxy,         2,2,2-trichloroethoxy, pentafluoroethoxy, 2-fluoropropoxy,         3-fluoropropoxy, 2-chloropropoxy, 3-chloropropoxy,         2-bromopropoxy, 3-bromopropoxy, 2,2-difluoropropoxy,         2,3-difluoropropoxy, 2,3-dichloropropoxy,         3,3,3-trifluoropropoxy, 3,3,3-trichloropropoxy,         2,2,3,3,3-pentafluoropropoxy, heptafluoropropoxy,         1-(fluoromethyl)-2-fluoroethoxy,         1-(chloromethyl)-2-chloroethoxy, 1-(bromomethyl)-2-bromoethoxy,         4-fluorobutoxy, 4-chlorobutoxy, 4-bromobutoxy or         nonafluorobutoxy;     -   C₁-C₆-haloalkoxy: C₁-C₄-haloalkoxy as mentioned above, and also,         for example, 5-fluoropentoxy, 5-chloropentoxy, 5-bromopentoxy,         5-iodopentoxy, undecafluoropentoxy, 6-fluorohexoxy,         6-chlorohexoxy, 6-bromohexoxy, 6-iodohexoxy or         dodecafluorohexoxy;     -   C₁-C₄-alkylthio: for example methylthio, ethylthio, propylthio,         1-methylethylthio, butylthio, 1-methylpropylthio,         2-methylpropylthio or 1,1-dimethylethylthio;     -   C₁-C₆-alkylthio, and the alkylthio moieties of         C₁-C₆-alkylthiocarbonyl: C₁-C₄-alkylthio as mentioned above and         also, for example, pentylthio, 1-methylbutylthio,         2-methylbutylthio, 3-methylbutylthio, 2,2-dimethylpropylthio,         1-ethylpropylthio, hexylthio, 1,1-dimethylpropylthio,         1,2-dimethylpropylthio, 1-methylpentylthio, 2-methylpentylthio,         3-methylpentylthio, 4-methylpentylthio, 1,1-dimethylbutylthio,         1,2-dimethylbutylthio, 1,3-dimethylbutylthio,         2,2-dimethylbutylthio, 2,3-dimethylbutylthio,         3,3-dimethylbutylthio, 1-ethylbutylthio, 2-ethylbutylthio,         1,1,2-trimethylpropylthio, 1,2,2-trimethylpropylthio,         1-ethyl-1-methylpropylthio or 1-ethyl-2-methylpropylthio;     -   C₁-C₆-haloalkylthio: a C₁-C₆-alkylthio radical as mentioned         above which is partially or fully substituted by fluorine,         chlorine, bromine and/or iodine, i.e., for example,         fluoromethylthio, difluoromethylthio, trifluoromethylthio,         chlorodifluoromethylthio, bromodifluoromethylthio,         2-fluoroethylthio, 2-chloroethylthio, 2-bromoethylthio,         2-iodoethylthio, 2,2-difluoroethylthio,         2,2,2-trifluoroethylthio, 2,2,2-trichloroethylthio,         2-chloro-2-fluoroethylthio, 2-chloro-2,2-difluoroethylthio,         2,2-dichloro-2-fluoroethylthio, pentafluoroethylthio,         2-fluoropropylthio, 3-fluoropropylthio, 2-chloropropylthio,         3-chloropropylthio, 2-bromopropylthio, 3-bromopropylthio,         2,2-difluoropropylthio, 2,3-difluoropropylthio,         2,3-dichloropropylthio, 3,3,3-trifluoropropylthio,         3,3,3-trichloropropylthio, 2,2,3,3,3-pentafluoropropylthio,         heptafluoropropylthio, 1-(fluoromethyl)-2-fluoroethylthio,         1-(chloromethyl)-2-chloroethylthio,         1-(bromomethyl)-2-bromoethylthio, 4-fluorobutylthio,         4-chlorobutylthio, 4-bromobutylthio, nonafluorobutylthio,         5-fluoropentylthio, 5-chloropentylthio, 5-bromopentylthio,         5-iodopentylthio, undecafluoropentylthio, 6-fluorohexylthio,         6-chlorohexylthio, 6-bromohexylthio, 6-iodohexylthio or         dodecafluorohexylthio;     -   C₁-C₆-alkylsulfinyl (C₁-C₆-alkyl-S(═O)—): for example         methylsulfinyl, ethylsulfinyl, propylsulfinyl,         1-methylethylsulfinyl, butylsulfinyl, 1-methylpropylsulfinyl,         2-methylpropylsulfinyl, 1,1-dimethylethylsulfinyl,         pentylsulfinyl, 1-methylbutylsulfinyl, 2-methylbutylsulfinyl,         3-methylbutylsulfinyl, 2,2-dimethylpropylsulfinyl,         1-ethylpropylsulfinyl, 1,1-dimethylpropylsulfinyl,         1,2-dimethylpropylsulfinyl, hexylsulfinyl,         1-methylpentylsulfinyl, 2-methylpentylsulfinyl,         3-methylpentylsulfinyl, 4-methylpentylsulfinyl,         1,1-dimethylbutylsulfinyl, 1,2-dimethylbutylsulfinyl,         1,3-dimethylbutylsulfinyl, 2,2-dimethylbutylsulfinyl,         2,3-dimethylbutylsulfinyl, 3,3-dimethylbutylsulfinyl,         1-ethylbutylsulfinyl, 2-ethylbutylsulfinyl,         1,1,2-trimethylpropylsulfinyl, 1,2,2-trimethylpropylsulfinyl,         1-ethyl-1-methylpropylsulfinyl or         1-ethyl-2-methylpropylsulfinyl;     -   C₁-C₆-haloalkylsulfinyl: a C₁-C₆-alkylsulfinyl radical as         mentioned above which is partially or fully substituted by         fluorine, chlorine, bromine and/or iodine, i.e., for example,         fluoromethylsulfinyl, difluoromethylsulfinyl,         trifluoromethylsulfinyl, chlorodifluoromethylsulfinyl,         bromodifluoromethylsulfinyl, 2-fluoroethylsulfinyl,         2-chloroethylsulfinyl, 2-bromoethylsulfinyl,         2-iodoethylsulfinyl, 2,2-difluoroethylsulfinyl,         2,2,2-trifluoroethylsulfinyl, 2,2,2-trichloroethylsulfinyl,         2-chloro-2-fluoroethylsulfinyl,         2-chloro-2,2-difluoroethylsulfinyl,         2,2-dichloro-2-fluoroethylsulfinyl, pentafluoroethylsulfinyl,         2-fluoropropylsulfinyl, 3-fluoropropylsulfinyl,         2-chloropropylsulfinyl, 3-chloropropylsulfinyl,         2-bromopropylsulfinyl, 3-bromopropylsulfinyl,         2,2-difluoropropylsulfinyl, 2,3-difluoropropylsulfinyl,         2,3-dichloropropylsulfinyl, 3,3,3-trifluoropropylsulfinyl,         3,3,3-trichloropropylsulfinyl,         2,2,3,3,3-pentafluoropropylsulfinyl, heptafluoropropylsulfinyl,         1-(fluoromethyl)-2-fluoroethylsulfinyl,         1-(chloromethyl)-2-chloroethylsulfinyl,         1-(bromomethyl)-2-bromoethylsulfinyl, 4-fluorobutylsulfinyl,         4-chlorobutylsulfinyl, 4-bromobutylsulfinyl,         nonafluorobutylsulfinyl, 5-fluoropentylsulfinyl,         5-chloropentylsulfinyl, 5-bromopentylsulfinyl,         5-iodopentylsulfinyl, undecafluoropentylsulfinyl,         6-fluorohexylsulfinyl, 6-chlorohexylsulfinyl,         6-bromohexylsulfinyl, 6-iodohexylsulfinyl or         dodecafluorohexylsulfinyl;     -   C₁-C₆-alkylsulfonyl (C₁-C₆-alkyl-S(═O)₂—), and the alkylsulfonyl         radicals of N—(C₁-C₆-alkylsulfonyl)amino and         N—(C₁-C₆-alkyl)-N—(C₁-C₆-alkylsulfonyl)amino: for example         methylsulfonyl, ethylsulfonyl, propylsulfonyl,         1-methylethylsulfonyl, butylsulfonyl, 1-methylpropylsulfonyl,         2-methylpropylsulfonyl, 1,1-dimethylethylsulfonyl,         pentylsulfonyl, 1-methylbutylsulfonyl, 2-methylbutylsulfonyl,         3-methylbutylsulfonyl, 1,1-dimethylpropylsulfonyl,         1,2-dimethylpropylsulfonyl, 2,2-dimethylpropylsulfonyl,         1-ethylpropylsulfonyl, hexylsulfonyl, 1-methylpentylsulfonyl,         2-methylpentylsulfonyl, 3-methylpentylsulfonyl,         4-methylpentylsulfonyl, 1,1-dimethylbutylsulfonyl,         1,2-dimethylbutylsulfonyl, 1,3-dimethylbutylsulfonyl,         2,2-dimethylbutylsulfonyl, 2,3-dimethylbutylsulfonyl,         3,3-dimethylbutylsulfonyl, 1-ethylbutylsulfonyl,         2-ethylbutylsulfonyl, 1,1,2-trimethylpropylsulfonyl,         1,2,2-trimethylpropylsulfonyl, 1-ethyl-1-methylpropylsulfonyl or         1-ethyl-2-methylpropylsulfonyl;     -   C₁-C₆-haloalkylsulfonyl, and the haloalkylsulfonyl radicals of         N—(C₁-C₆-haloalkylsulfonyl)amino and         N—(C₁-C₆-alkyl)-N—(C₁-C₆-haloalkylsulfonyl)amino: a         C₁-C₆-alkylsulfonyl radical as mentioned above which is         partially or fully substituted by fluorine, chlorine, bromine         and/or iodine, i.e., for example, fluoromethylsulfonyl,         difluoromethylsulfonyl, trifluoromethylsulfonyl,         chlorodifluoromethylsulfonyl, bromodifluoromethylsulfonyl,         2-fluoroethylsulfonyl, 2-chloroethylsulfonyl,         2-bromoethylsulfonyl, 2-iodoethylsulfonyl,         2,2-difluoroethylsulfonyl, 2,2,2-trifluoroethylsulfonyl,         2-chloro-2-fluoroethylsulfonyl,         2-chloro-2,2-difluoroethylsulfonyl,         2,2-dichloro-2-fluoroethylsulfonyl,         2,2,2-trichloroethylsulfonyl, pentafluoroethylsulfonyl,         2-fluoropropylsulfonyl, 3-fluoropropylsulfonyl,         2-chloropropylsulfonyl, 3-chloropropylsulfonyl,         2-bromopropylsulfonyl, 3-bromopropylsulfonyl,         2,2-difluoropropylsulfonyl, 2,3-difluoropropylsulfonyl,         2,3-dichloropropylsulfonyl, 3,3,3-trifluoropropylsulfonyl,         3,3,3-trichloropropylsulfonyl,         2,2,3,3,3-pentafluoropropylsulfonyl, heptafluoropropylsulfonyl,         1-(fluoromethyl)-2-fluoroethylsulfonyl,         1-(chloromethyl)-2-chloroethylsulfonyl,         1-(bromomethyl)-2-bromoethylsulfonyl, 4-fluorobutylsulfonyl,         4-chlorobutylsulfonyl, 4-bromobutylsulfonyl,         nonafluorobutylsulfonyl, 5-fluoropentylsulfonyl,         5-chloropentylsulfonyl, 5-bromopentylsulfonyl,         5-iodopentylsulfonyl, 6-fluorohexylsulfonyl,         6-bromohexylsulfonyl, 6-iodohexylsulfonyl or         dodecafluorohexylsulfonyl;     -   C₁-C₆-alkylamino, and the alkylamino radicals of         N—(C₁-C₆-alkylamino)imino-C₁-C₆-alkyl: for example methylamino,         ethylamino, propylamino, 1-methylethylamino, butylamino,         1-methylpropylamino, 2-methylpropylamino,         1,1-dimethylethylamino, pentylamino, 1-methylbutylamino,         2-methylbutylamino, 3-methylbutylamino, 2,2-dimethylpropylamino,         1-ethylpropylamino, hexylamino, 1,1-dimethylpropylamino,         1,2-dimethylpropylamino, 1-methylpentylamino,         2-methylpentylamino, 3-methylpentylamino, 4-methylpentylamino,         1,1-dimethylbutylamino, 1,2-dimethylbutylamino,         1,3-dimethylbutylamino, 2,2-dimethylbutylamino,         2,3-dimethylbutylamino, 3,3-dimethylbutylamino,         1-ethylbutylamino, 2-ethylbutylamino,         1,1,2-trimethylpropylamino, 1,2,2-trimethylpropylamino,         1-ethyl-1-methylpropylamino or 1-ethyl-2-methylpropylamino;     -   (C₁-C₆-alkylamino)sulfonyl: for example methylaminosulfonyl,         ethylaminosulfonyl, propylaminosulfonyl,         1-methylethylaminosulfonyl, butylaminosulfonyl,         1-methylpropylaminosulfonyl, 2-methylpropylaminosulfonyl,         1,1-dimethylethylaminosulfonyl, pentylaminosulfonyl,         1-methylbutylaminosulfonyl, 2-methylbutylaminosulfonyl,         3-methylbutylaminosulfonyl, 2,2-dimethylpropylaminosulfonyl,         1-ethylpropylaminosulfonyl, hexylaminosulfonyl,         1,1-dimethylpropylaminosulfonyl,         1,2-dimethylpropylaminosulfonyl, 1-methylpentylaminosulfonyl,         2-methylpentylaminosulfonyl, 3-methylpentylaminosulfonyl,         4-methylpentylaminosulfonyl, 1,1-dimethylbutylaminosulfonyl,         1,2-dimethylbutylaminosulfonyl, 1,3-dimethylbutylaminosulfonyl,         2,2-dimethylbutylaminosulfonyl, 2,3-dimethylbutylaminosulfonyl,         3,3-dimethylbutylaminosulfonyl, 1-ethylbutylaminosulfonyl,         2-ethylbutylaminosulfonyl, 1,1,2-trimethylpropylaminosulfonyl,         1,2,2-trimethylpropylaminosulfonyl,         1-ethyl-1-methylpropylaminosulfonyl or         1-ethyl-2-methylpropylaminosulfonyl;     -   di(C₁-C₆-alkyl)aminosulfonyl: for example         N,N-dimethylaminosulfonyl, N,N-diethylaminosulfonyl,         N,N-di(1-methylethyl)aminosulfonyl, N,N-dipropylaminosulfonyl,         N,N-dibutylaminosulfonyl, N,N-di(1-methylpropyl)aminosulfonyl,         N,N-di(2-methylpropyl)aminosulfonyl,         N,N-di(1,1-dimethylethyl)aminosulfonyl,         N-ethyl-N-methylaminosulfonyl, N-methyl-N-propylaminosulfonyl,         N-methyl-N-(1-methylethyl)aminosulfonyl,         N-butyl-N-methylaminosulfonyl,         N-methyl-N-(1-methylpropyl)aminosulfonyl,         N-methyl-N-(2-methylpropyl)aminosulfonyl,         N-(1,1-dimethylethyl)-N-methylaminosulfonyl,         N-ethyl-N-propylaminosulfonyl,         N-ethyl-N-(1-methylethyl)aminosulfonyl,         N-butyl-N-ethylaminosulfonyl,         N-ethyl-N-(1-methylpropyl)aminosulfonyl,         N-ethyl-N-(2-methylpropyl)aminosulfonyl,         N-ethyl-N-(1,1-dimethylethyl)aminosulfonyl,         N-(1-methylethyl)-N-propylaminosulfonyl,         N-butyl-N-propylaminosulfonyl,         N-(1-methylpropyl)-N-propylaminosulfonyl,         N-(2-methylpropyl)-N-propylaminosulfonyl,         N-(1,1-dimethylethyl)-N-propylaminosulfonyl,         N-butyl-N-(1-methylethyl)aminosulfonyl,         N-(1-methylethyl)-N-(1-methylpropyl)aminosulfonyl,         N-(1-methylethyl)-N-(2-methylpropyl)aminosulfonyl,         N-(1,1-dimethylethyl)-N-(1-methylethyl)aminosulfonyl,         N-butyl-N-(1-methylpropyl)aminosulfonyl,         N-butyl-N-(2-methylpropyl)aminosulfonyl,         N-butyl-N-(1,1-dimethylethyl)aminosulfonyl,         N-(1-methylpropyl)-N-(2-methylpropyl)aminosulfonyl,         N-(1,1-dimethylethyl)-N-(1-methylpropyl)aminosulfonyl,         N-(1,1-dimethylethyl)-N-(2-methylpropyl)aminosulfonyl,         N-methyl-N-pentylaminosulfonyl,         N-methyl-N-(1-methylbutyl)aminosulfonyl,         N-methyl-N-(2-methylbutyl)aminosulfonyl,         N-methyl-N-(3-methylbutyl)aminosulfonyl,         N-methyl-N-(2,2-dimethylpropyl)aminosulfonyl,         N-methyl-N-(1-ethylpropyl)aminosulfonyl,         N-methyl-N-hexylaminosulfonyl,         N-methyl-N-(1,1-dimethylpropyl)aminosulfonyl,         N-methyl-N-(1,2-dimethylpropyl)aminosulfonyl,         N-methyl-N-(1-methylpentyl)aminosulfonyl,         N-methyl-N-(2-methylpentyl)aminosulfonyl,         N-methyl-N-(3-methylpentyl)aminosulfonyl,         N-methyl-N-(4-methylpentyl)aminosulfonyl,         N-methyl-N-(1,1-dimethylbutyl)aminosulfonyl,         N-methyl-N-(1,2-dimethylbutyl)aminosulfonyl,         N-methyl-N-(1,3-dimethylbutyl)aminosulfonyl,         N-methyl-N-(2,2-dimethylbutyl)aminosulfonyl,         N-methyl-N-(2,3-dimethylbutyl)aminosulfonyl,         N-methyl-N-(3,3-dimethylbutyl)aminosulfonyl,         N-methyl-N-(1-ethylbutyl)aminosulfonyl,         N-methyl-N-(2-ethylbutyl)aminosulfonyl,         N-methyl-N-(1,1,2-trimethylpropyl)aminosulfonyl,         N-methyl-N-(1,2,2-trimethylpropyl)aminosulfonyl,         N-methyl-N-(1-ethyl-1-methylpropyl)aminosulfonyl,         N-methyl-N-(1-ethyl-2-methylpropyl)aminosulfonyl,         N-ethyl-N-pentylaminosulfonyl,         N-ethyl-N-(1-methylbutyl)aminosulfonyl,         N-ethyl-N-(2-methylbutyl)aminosulfonyl,         N-ethyl-N-(3-methylbutyl)aminosulfonyl,         N-ethyl-N-(2,2-dimethylpropyl)aminosulfonyl,         N-ethyl-N-(1-ethylpropyl)aminosulfonyl,         N-ethyl-N-hexylaminosulfonyl,         N-ethyl-N-(1,1-dimethylpropyl)aminosulfonyl,         N-ethyl-N-(1,2-dimethylpropyl)aminosulfonyl,         N-ethyl-N-(1-methylpentyl)aminosulfonyl,         N-ethyl-N-(2-methylpentyl)aminosulfonyl,         N-ethyl-N-(3-methylpentyl)aminosulfonyl,         N-ethyl-N-(4-methylpentyl)aminosulfonyl,         N-ethyl-N-(1,1-dimethylbutyl)aminosulfonyl,         N-ethyl-N-(1,2-dimethylbutyl)aminosulfonyl,         N-ethyl-N-(1,3-dimethylbutyl)aminosulfonyl,         N-ethyl-N-(2,2-dimethylbutyl)aminosulfonyl,         N-ethyl-N-(2,3-dimethylbutyl)aminosulfonyl,         N-ethyl-N-(3,3-dimethylbutyl)aminosulfonyl,         N-ethyl-N-(1-ethylbutyl)aminosulfonyl,         N-ethyl-N-(2-ethylbutyl)aminosulfonyl,         N-ethyl-N-(1,1,2-trimethylpropyl)aminosulfonyl,         N-ethyl-N-(1,2,2-trimethylpropyl)aminosulfonyl,         N-ethyl-N-(1-ethyl-1-methylpropyl)aminosulfonyl,         N-ethyl-N-(1-ethyl-2-methylpropyl)aminosulfonyl,         N-propyl-N-pentylaminosulfonyl, N-butyl-N-pentylaminosulfonyl,         N,N-dipentylaminosulfonyl, N-propyl-N-hexylaminosulfonyl,         N-butyl-N-hexylaminosulfonyl, N-pentyl-N-hexylaminosulfonyl or         N,N-dihexylaminosulfonyl;     -   di(C₁-C₄-alkyl)amino, and the dialkylamino radicals of         di(C₁-C₄-alkyl)amino-C₁-C₄-alkoxycarbonyl and         N-(di-C₁-C₄-alkylamino)imino-C₁-C₆-alkyl: for example         N,N-dimethylamino, N,N-diethylamino, N,N-dipropylamino,         N,N-di(1-methylethyl)amino, N,N-dibutylamino,         N,N-di(1-methylpropyl)amino, N,N-di(2-methylpropyl)amino,         N,N-di(1,1-dimethylethyl)amino, N-ethyl-N-methylamino,         N-methyl-N-propylamino, N-methyl-N-(1-methylethyl)amino,         N-butyl-N-methylamino, N-methyl-N-(1-methylpropyl)amino,         N-methyl-N-(2-methylpropyl)amino,         N-(1,1-dimethylethyl)-N-methylamino, N-ethyl-N-propylamino,         N-ethyl-N-(1-methylethyl)amino, N-butyl-N-ethylamino,         N-ethyl-N-(1-methylpropyl)amino,         N-ethyl-N-(2-methylpropyl)amino,         N-ethyl-N-(1,1-dimethylethyl)amino,         N-(1-methylethyl)-N-propylamino, N-butyl-N-propylamino,         N-(1-methylpropyl)-N-propylamino,         N-(2-methylpropyl)-N-propylamino,         N-(1,1-dimethylethyl)-N-propylamino,         N-butyl-N-(1-methylethyl)amino,         N-(1-methylethyl)-N-(1-methylpropyl)amino,         N-(1-methylethyl)-N-(2-methylpropyl)amino,         N-(1,1-dimethylethyl)-N-(1-methylethyl)amino,         N-butyl-N-(1-methylpropyl)amino,         N-butyl-N-(2-methylpropyl)amino,         N-butyl-N-(1,1-dimethylethyl)amino,         N-(1-methylpropyl)-N-(2-methylpropyl)amino,         N-(1,1-dimethylethyl)-N-(1-methylpropyl)amino or         N-(1,1-dimethylethyl)-N-(2-methylpropyl)amino;     -   di(C₁-C₆-alkyl)amino, and the dialkylamino radicals of         di(C₁-C₆-alkyl)aminoimino-C₁-C₆-alkyl: di(C₁-C₄-alkyl)amino as         mentioned above, and also N,N-dipentylamino, N,N-dihexylamino,         N-methyl-N-pentylamino, N-ethyl-N-pentylamino,         N-methyl-N-hexylamino or N-ethyl-N-hexylamino;     -   C₁-C₄-alkylcarbonyl: for example methylcarbonyl, ethylcarbonyl,         propylcarbonyl, 1-methylethylcarbonyl, butylcarbonyl,         1-methylpropylcarbonyl, 2-methylpropylcarbonyl or         1,1-dimethylethylcarbonyl;     -   C₁-C₆-alkylcarbonyl, and the alkylcarbonyl radicals of         C₁-C₆-alkylcarbonyl-C₁-C₆-alkyl: C₁-C₄-alkylcarbonyl as         mentioned above, and also, for example, pentylcarbonyl,         1-methylbutylcarbonyl, 2-methylbutylcarbonyl,         3-methylbutylcarbonyl, 2,2-dimethylpropylcarbonyl,         1-ethylpropylcarbonyl, hexylcarbonyl,         1,1-dimethylpropylcarbonyl, 1,2-dimethylpropylcarbonyl,         1-methylpentylcarbonyl, 2-methylpentylcarbonyl,         3-methylpentylcarbonyl, 4-methylpentylcarbonyl,         1,1-dimethylbutylcarbonyl, 1,2-dimethylbutylcarbonyl,         1,3-dimethylbutylcarbonyl, 2,2-dimethylbutylcarbonyl,         2,3-dimethylbutylcarbonyl, 3,3-dimethylbutylcarbonyl,         1-ethylbutylcarbonyl, 2-ethylbutylcarbonyl,         1,1,2-trimethylpropylcarbonyl, 1,2,2-trimethylpropylcarbonyl,         1-ethyl-1-methylpropylcarbonyl or         1-ethyl-2-methylpropylcarbonyl;     -   C₁-C₂₀-alkylcarbonyl: C₁-C₆-alkylcarbonyl as mentioned above,         and also heptylcarbonyl, octylcarbonyl, pentadecylcarbonyl or         heptadecylcarbonyl;     -   C₁-C₄-alkoxycarbonyl, and the alkoxycarbonyl moieties of         di(C₁-C₄-alkyl)amino-C₁-C₄-alkoxycarbonyl: for example         methoxycarbonyl, ethoxycarbonyl, propoxycarbonyl,         1-methylethoxycarbonyl, butoxycarbonyl, 1-methylpropoxycarbonyl,         2-methylpropoxycarbonyl or 1,1-dimethylethoxycarbonyl;     -   (C₁-C₆-alkoxy)carbonyl: (C₁-C₄-alkoxy)carbonyl as mentioned         above, and also, for example, pentoxycarbonyl,         1-methylbutoxycarbonyl, 2-methylbutoxycarbonyl,         3-methylbutoxycarbonyl, 2,2-dimethylpropoxycarbonyl,         1-ethylpropoxycarbonyl, hexoxycarbonyl,         1,1-dimethylpropoxycarbonyl, 1,2-dimethylpropoxycarbonyl,         1-methylpentoxycarbonyl, 2-methylpentoxycarbonyl,         3-methylpentoxycarbonyl, 4-methylpentoxycarbonyl,         1,1-dimethylbutoxycarbonyl, 1,2-dimethylbutoxycarbonyl,         1,3-dimethylbutoxycarbonyl, 2,2-dimethylbutoxycarbonyl,         2,3-dimethylbutoxycarbonyl, 3,3-dimethylbutoxycarbonyl,         1-ethylbutoxycarbonyl, 2-ethylbutoxycarbonyl,         1,1,2-trimethylpropoxycarbonyl, 1,2,2-trimethylpropoxycarbonyl,         1-ethyl-1-methyl-propoxycarbonyl or         1-ethyl-2-methyl-propoxycarbonyl;     -   C₁-C₆-haloalkoxycarbonyl: a C₁-C₆-alkoxycarbonyl radical as         mentioned above which is partially or fully substituted by         fluorine, chlorine, bromine and/or iodine, i.e., for example,         fluoromethoxycarbonyl, difluoromethoxycarbonyl,         trifluoromethoxycarbonyl, chlorodifluoromethoxycarbonyl,         bromodifluoromethoxycarbonyl, 2-fluoroethoxycarbonyl,         2-chloroethoxycarbonyl, 2-bromoethoxycarbonyl,         2-iodoethoxycarbonyl, 2,2-difluoroethoxycarbonyl,         2,2,2-trifluoroethoxycarbonyl, 2-chloro-2-fluoroethoxycarbonyl,         2-chloro-2,2-difluoroethoxycarbonyl,         2,2-dichloro-2-fluoroethoxycarbonyl,         2,2,2-trichloroethoxycarbonyl, pentafluoroethoxycarbonyl,         2-fluoropropoxycarbonyl, 3-fluoropropoxycarbonyl,         2-chloropropoxycarbonyl, 3-chloropropoxycarbonyl,         2-bromopropoxycarbonyl, 3-bromopropoxycarbonyl,         2,2-difluoropropoxycarbonyl, 2,3-difluoropropoxycarbonyl,         2,3-dichloropropoxycarbonyl, 3,3,3-trifluoropropoxycarbonyl,         3,3,3-trichloropropoxycarbonyl,         2,2,3,3,3-pentafluoropropoxycarbonyl,         heptafluoropropoxycarbonyl,         1-(fluoromethyl)-2-fluoroethoxycarbonyl,         1-(chloromethyl)-2-chloroethoxycarbonyl,         1-(bromomethyl)-2-bromoethoxycarbonyl, 4-fluorobutoxycarbonyl,         4-chlorobutoxycarbonyl, 4-bromobutoxycarbonyl,         nonafluorobutoxycarbonyl, 5-fluoropentoxycarbonyl,         5-chloropentoxycarbonyl, 5-bromopentoxycarbonyl,         5-iodopentoxycarbonyl, 6-fluorohexoxycarbonyl,         6-bromohexoxycarbonyl, 6-iodohexoxycarbonyl or         dodecafluorohexoxycarbonyl;     -   (C₁-C₄-alkyl)carbonyloxy: acetyloxy, ethylcarbonyloxy,         propylcarbonyloxy, 1-methylethylcarbonyloxy, butylcarbonyloxy,         1-methylpropylcarbonyloxy, 2-methylpropylcarbonyloxy or         1,1-dimethylethylcarbonyloxy;     -   (C₁-C₄-alkylamino)carbonyl: for example methylaminocarbonyl,         ethylaminocarbonyl, propylaminocarbonyl,         1-methylethylaminocarbonyl, butylaminocarbonyl,         1-methylpropylaminocarbonyl, 2-methylpropylaminocarbonyl or         1,1-dimethylethylaminocarbonyl;     -   (C₁-C₆-alkylamino)carbonyl: (C₁-C₄-alkylamino)carbonyl as         mentioned above, and also, for example, pentylaminocarbonyl,         1-methylbutylaminocarbonyl, 2-methylbutylaminocarbonyl,         3-methylbutylaminocarbonyl, 2,2-dimethylpropylaminocarbonyl,         1-ethylpropylaminocarbonyl, hexylaminocarbonyl,         1,1-dimethylpropylaminocarbonyl,         1,2-dimethylpropylaminocarbonyl, 1-methylpentylaminocarbonyl,         2-methylpentylaminocarbonyl, 3-methylpentylaminocarbonyl,         4-methylpentylaminocarbonyl, 1,1-dimethylbutylaminocarbonyl,         1,2-dimethylbutylaminocarbonyl, 1,3-dimethylbutylaminocarbonyl,         2,2-dimethylbutylaminocarbonyl, 2,3-dimethylbutylaminocarbonyl,         3,3-dimethylbutylaminocarbonyl, 1-ethylbutylaminocarbonyl,         2-ethylbutylaminocarbonyl, 1,1,2-trimethylpropylaminocarbonyl,         1,2,2-trimethylpropylaminocarbonyl,         1-ethyl-1-methylpropylaminocarbonyl or         1-ethyl-2-methylpropylaminocarbonyl;     -   di(C₁-C₄-alkyl)aminocarbonyl: for example         N,N-dimethylaminocarbonyl, N,N-diethylaminocarbonyl,         N,N-di(1-methylethyl)aminocarbonyl, N,N-dipropylaminocarbonyl,         N,N-dibutylaminocarbonyl, N,N-di(1-methylpropyl)aminocarbonyl,         N,N-di(2-methylpropyl)aminocarbonyl,         N,N-di(1,1-dimethylethyl)aminocarbonyl,         N-ethyl-N-methylaminocarbonyl, N-methyl-N-propylaminocarbonyl,         N-methyl-N-(1-methylethyl)aminocarbonyl,         N-butyl-N-methylaminocarbonyl,         N-methyl-N-(1-methylpropyl)aminocarbonyl,         N-methyl-N-(2-methylpropyl)aminocarbonyl,         N-(1,1-dimethylethyl)-N-methylaminocarbonyl,         N-ethyl-N-propylaminocarbonyl,         N-ethyl-N-(1-methylethyl)aminocarbonyl,         N-butyl-N-ethylaminocarbonyl,         N-ethyl-N-(1-methylpropyl)aminocarbonyl,         N-ethyl-N-(2-methylpropyl)aminocarbonyl,         N-ethyl-N-(1,1-dimethylethyl)aminocarbonyl,         N-(1-methylethyl)-N-propylaminocarbonyl,         N-butyl-N-propylaminocarbonyl,         N-(1-methylpropyl)-N-propylaminocarbonyl,         N-(2-methylpropyl)-N-propylaminocarbonyl,         N-(1,1-dimethylethyl)-N-propylaminocarbonyl,         N-butyl-N-(1-methylethyl)aminocarbonyl,         N-(1-methylethyl)-N-(1-methylpropyl)aminocarbonyl,         N-(1-methylethyl)-N-(2-methylpropyl)aminocarbonyl,         N-(1,1-dimethylethyl)-N-(1-methylethyl)aminocarbonyl,         N-butyl-N-(1-methylpropyl)aminocarbonyl,         N-butyl-N-(2-methylpropyl)aminocarbonyl,         N-butyl-N-(1,1-dimethylethyl)aminocarbonyl,         N-(1-methylpropyl)-N-(2-methylpropyl)aminocarbonyl,         N-(1,1-dimethylethyl)-N-(1-methylpropyl)aminocarbonyl or         N-(1,1-dimethylethyl)-N-(2-methylpropyl)aminocarbonyl;     -   di(C₁-C₆-alkyl)aminocarbonyl: di(C₁-C₄-alkyl)aminocarbonyl as         mentioned above, and also, for example,         N-methyl-N-pentylaminocarbonyl,         N-methyl-N-(1-methylbutyl)aminocarbonyl,         N-Methyl-N-(2-methylbutyl)aminocarbonyl,         N-methyl-N-(3-methylbutyl)aminocarbonyl,         N-methyl-N-(2,2-dimethylpropyl)aminocarbonyl,         N-methyl-N-(1-ethylpropyl)aminocarbonyl,         N-methyl-N-hexylaminocarbonyl,         N-methyl-N-(1,1-dimethylpropyl)aminocarbonyl,         N-methyl-N-(1,2-dimethylpropyl)aminocarbonyl,         N-methyl-N-(1-methylpentyl)aminocarbonyl,         N-methyl-N-(2-methylpentyl)aminocarbonyl,         N-methyl-N-(3-methylpentyl)aminocarbonyl,         N-methyl-N-(4-methylpentyl)aminocarbonyl,         N-methyl-N-(1,1-dimethylbutyl)aminocarbonyl,         N-methyl-N-(1,2-dimethylbutyl)aminocarbonyl,         N-methyl-N-(1,3-dimethylbutyl)aminocarbonyl,         N-methyl-N-(2,2-dimethylbutyl)aminocarbonyl,         N-methyl-N-(2,3-dimethylbutyl)aminocarbonyl,         N-methyl-N-(3,3-dimethylbutyl)aminocarbonyl,         N-methyl-N-(1-ethylbutyl)aminocarbonyl,         N-methyl-N-(2-ethylbutyl)aminocarbonyl,         N-methyl-N-(1,1,2-trimethylpropyl)aminocarbonyl,         N-methyl-N-(1,2,2-trimethylpropyl)aminocarbonyl,         N-methyl-N-(1-ethyl-1-methylpropyl)aminocarbonyl,         N-methyl-N-(1-ethyl-2-methylpropyl)aminocarbonyl,         N-ethyl-N-pentylaminocarbonyl,         N-ethyl-N-(1-methylbutyl)aminocarbonyl,         N-ethyl-N-(2-methylbutyl)aminocarbonyl,         N-ethyl-N-(3-methylbutyl)aminocarbonyl,         N-ethyl-N-(2,2-dimethylpropyl)aminocarbonyl,         N-ethyl-N-(1-ethylpropyl)aminocarbonyl,         N-ethyl-N-hexylaminocarbonyl,         N-ethyl-N-(1,1-dimethylpropyl)aminocarbonyl,         N-ethyl-N-(1,2-dimethylpropyl)aminocarbonyl,         N-ethyl-N-(1-methylpentyl)aminocarbonyl,         N-ethyl-N-(2-methylpentyl)aminocarbonyl,         N-ethyl-N-(3-methylpentyl)aminocarbonyl,         N-ethyl-N-(4-methylpentyl)aminocarbonyl,         N-ethyl-N-(1,1-dimethylbutyl)aminocarbonyl,         N-ethyl-N-(1,2-dimethylbutyl)aminocarbonyl,         N-ethyl-N-(1,3-dimethylbutyl)aminocarbonyl,         N-ethyl-N-(2,2-dimethylbutyl)aminocarbonyl,         N-ethyl-N-(2,3-dimethylbutyl)aminocarbonyl,         N-ethyl-N-(3,3-dimethylbutyl)aminocarbonyl,         N-ethyl-N-(1-ethylbutyl)aminocarbonyl,         N-ethyl-N-(2-ethylbutyl)aminocarbonyl,         N-ethyl-N-(1,1,2-trimethylpropyl)aminocarbonyl,         N-ethyl-N-(1,2,2-trimethylpropyl)aminocarbonyl,         N-ethyl-N-(1-ethyl-1-methylpropyl)aminocarbonyl,         N-ethyl-N-(1-ethyl-2-methylpropyl)aminocarbonyl,         N-propyl-N-pentylaminocarbonyl, N-butyl-N-pentylaminocarbonyl,         N,N-dipentylaminocarbonyl, N-propyl-N-hexylaminocarbonyl,         N-butyl-N-hexylaminocarbonyl, N-pentyl-N-hexylaminocarbonyl or         N,N-dihexylaminocarbonyl;     -   di(C₁-C₆-alkyl)aminothiocarbonyl: for example         N,N-dimethylaminothiocarbonyl, N,N-diethylaminothiocarbonyl,         N,N-di(1-methylethyl)aminothiocarbonyl,         N,N-dipropylaminothiocarbonyl, N,N-dibutylaminothiocarbonyl,         N,N-di(1-methylpropyl)aminothiocarbonyl,         N,N-di(2-methylpropyl)aminothiocarbonyl,         N,N-di(1,1-dimethylethyl)aminothiocarbonyl,         N-ethyl-N-methylaminothiocarbonyl,         N-methyl-N-propylaminothiocarbonyl,         N-methyl-N-(1-methylethyl)aminothiocarbonyl,         N-butyl-N-methylaminothiocarbonyl,         N-methyl-N-(1-methylpropyl)aminothiocarbonyl,         N-methyl-N-(2-methylpropyl)aminothiocarbonyl,         N-(1,1-dimethylethyl)-N-methylaminothiocarbonyl,         N-ethyl-N-propylaminothiocarbonyl,         N-ethyl-N-(1-methylethyl)aminothiocarbonyl,         N-butyl-N-ethylaminothiocarbonyl,         N-ethyl-N-(1-methylpropyl)aminothiocarbonyl,         N-ethyl-N-(2-methylpropyl)aminothiocarbonyl,         N-ethyl-N-(1,1-dimethylethyl)aminothiocarbonyl,         N-(1-methylethyl)-N-propylaminothiocarbonyl,         N-butyl-N-propylaminothiocarbonyl,         N-(1-methylpropyl)-N-propylaminothiocarbonyl,         N-(2-methylpropyl)-N-propylaminothiocarbonyl,         N-(1,1-dimethylethyl)-N-propylaminothiocarbonyl,         N-butyl-N-(1-methylethyl)aminothiocarbonyl,         N-(1-methylethyl)-N-(1-methylpropyl)aminothiocarbonyl,         N-(1-methylethyl)-N-(2-methylpropyl)aminothiocarbonyl,         N-(1,1-dimethylethyl)-N-(1-methylethyl)aminothiocarbonyl,         N-butyl-N-(1-methylpropyl)aminothiocarbonyl,         N-butyl-N-(2-methylpropyl)aminothiocarbonyl,         N-butyl-N-(1,1-dimethylethyl)aminothiocarbonyl,         N-(1-methylpropyl)-N-(2-methylpropyl)aminothiocarbonyl,         N-(1,1-dimethylethyl)-N-(1-methylpropyl)aminothiocarbonyl,         N-(1,1-dimethylethyl)-N-(2-methylpropyl)aminothiocarbonyl,         N-methyl-N-pentylaminothiocarbonyl,         N-methyl-N-(1-methylbutyl)aminothiocarbonyl,         N-methyl-N-(2-methylbutyl)aminothiocarbonyl,         N-methyl-N-(3-methylbutyl)aminothiocarbonyl,         N-methyl-N-(2,2-dimethylpropyl)aminothiocarbonyl,         N-methyl-N-(1-ethylpropyl)aminothiocarbonyl,         N-methyl-N-hexylaminothiocarbonyl,         N-methyl-N-(1,1-dimethylpropyl)aminothiocarbonyl,         N-methyl-N-(1,2-dimethylpropyl)aminothiocarbonyl,         N-methyl-N-(1-methylpentyl)aminothiocarbonyl,         N-methyl-N-(2-methylpentyl)aminothiocarbonyl,         N-methyl-N-(3-methylpentyl)aminothiocarbonyl,         N-methyl-N-(4-methylpentyl)aminothiocarbonyl,         N-methyl-N-(1,1-dimethylbutyl)aminothiocarbonyl,         N-methyl-N-(1,2-dimethylbutyl)aminothiocarbonyl,         N-methyl-N-(1,3-dimethylbutyl)aminothiocarbonyl,         N-methyl-N-(2,2-dimethylbutyl)aminothiocarbonyl,         N-methyl-N-(2,3-dimethylbutyl)aminothiocarbonyl,         N-methyl-N-(3,3-dimethylbutyl)aminothiocarbonyl,         N-methyl-N-(1-ethylbutyl)aminothiocarbonyl,         N-methyl-N-(2-ethylbutyl)aminothiocarbonyl,         N-methyl-N-ethyl-N-(1,1,2-trimethylpropyl)aminothiocarbonyl,         N-methyl-N-(1,2,2-trimethylpropyl)aminothiocarbonyl,         N-methyl-N-(1-ethyl-1-methylpropyl)aminothiocarbonyl,         N-methyl-N-(1-ethyl-2-methylpropyl)aminothiocarbonyl,         N-ethyl-N-pentylaminothiocarbonyl,         N-ethyl-N-(1-methylbutyl)aminothiocarbonyl,         N-ethyl-N-(2-methylbutyl)aminothiocarbonyl,         N-ethyl-N-(3-methylbutyl)aminothiocarbonyl,         N-ethyl-N-(2,2-dimethylpropyl)aminothiocarbonyl,         N-ethyl-N-(1-ethylpropyl)aminothiocarbonyl,         N-ethyl-N-hexylaminothiocarbonyl,         N-ethyl-N-(1,1-dimethylpropyl)aminothiocarbonyl,         N-ethyl-N-(1,2-dimethylpropyl)aminothiocarbonyl,         N-ethyl-N-(1-methylpentyl)aminothiocarbonyl,         N-ethyl-N-(2-methylpentyl)aminothiocarbonyl,         N-ethyl-N-(3-methylpentyl)aminothiocarbonyl,         N-ethyl-N-(4-methylpentyl)aminothiocarbonyl,         N-ethyl-N-(1,1-dimethylbutyl)aminothiocarbonyl,         N-ethyl-N-(1,2-dimethylbutyl)aminothiocarbonyl,         N-ethyl-N-(1,3-dimethylbutyl)aminothiocarbonyl,         N-ethyl-N-(2,2-dimethylbutyl)aminothiocarbonyl,         N-ethyl-N-(2,3-dimethylbutyl)aminothiocarbonyl,         N-ethyl-N-(3,3-dimethylbutyl)aminothiocarbonyl,         N-ethyl-N-(1-ethylbutyl)aminothiocarbonyl,         N-ethyl-N-(2-ethylbutyl)aminothiocarbonyl,         N-ethyl-N-(1,1,2-trimethylpropyl)aminothiocarbonyl,         N-ethyl-N-(1,2,2-trimethylpropyl)aminothiocarbonyl,         N-ethyl-N-(1-ethyl-1-methylpropyl)aminothiocarbonyl,         N-ethyl-N-(1-ethyl-2-methylpropyl)aminothiocarbonyl,         N-propyl-N-pentylaminothiocarbonyl,         N-butyl-N-pentylaminothiocarbonyl,         N,N-dipentylaminothiocarbonyl,         N-propyl-N-hexylaminothiocarbonyl,         N-butyl-N-hexylaminothiocarbonyl,         N-pentyl-N-hexylaminothiocarbonyl or         N,N-dihexylaminothiocarbonyl;     -   C₁-C₄-alkoxy-C₁-C₄-alkyl and the alkoxyalkyl moieties of         hydroxy-C₁-C₄-alkoxy-C₁-C₄-alkyl: C₁-C₄-alkyl which is         substituted by C₁-C₄-alkoxy as mentioned above, i.e., for         example, methoxymethyl, ethoxymethyl, propoxymethyl,         (1-methylethoxy)methyl, butoxymethyl, (1-methylpropoxy)methyl,         (2-methylpropoxy)methyl, (1,1-dimethylethoxy)methyl,         2-(methoxy)ethyl, 2-(ethoxy)ethyl, 2-(propoxy)ethyl,         2-(1-methylethoxy)ethyl, 2-(butoxy)ethyl,         2-(1-methylpropoxy)ethyl, 2-(2-methylpropoxy)ethyl,         2-(1,1-dimethylethoxy)ethyl, 2-(methoxy)propyl,         2-(ethoxy)propyl, 2-(propoxy)propyl, 2-(1-methylethoxy)propyl,         2-(butoxy)propyl, 2-(1-methylpropoxy)propyl,         2-(2-methylpropoxy)propyl, 2-(1,1-dimethylethoxy)propyl,         3-(methoxy)propyl, 3-(ethoxy)propyl, 3-(propoxy)propyl,         3-(1-methylethoxy)propyl, 3-(butoxy)propyl,         3-(1-methylpropoxy)propyl, 3-(2-methylpropoxy)propyl,         3-(1,1-dimethylethoxy)propyl, 2-(methoxy)butyl, 2-(ethoxy)butyl,         2-(propoxy)butyl, 2-(1-methylethoxy)butyl, 2-(butoxy)butyl,         2-(1-methylpropoxy)butyl, 2-(2-methylpropoxy)butyl,         2-(1,1-dimethylethoxy)butyl, 3-(methoxy)butyl, 3-(ethoxy)butyl,         3-(propoxy)butyl, 3-(1-methylethoxy)butyl, 3-(butoxy)butyl,         3-(1-methylpropoxy)butyl, 3-(2-methylpropoxy)butyl,         3-(1,1-dimethylethoxy)butyl, 4-(methoxy)butyl, 4-(ethoxy)butyl,         4-(propoxy)butyl, 4-(1-methylethoxy)butyl, 4-(butoxy)butyl,         4-(1-methylpropoxy)butyl, 4-(2-methylpropoxy)butyl or         4-(1,1-dimethylethoxy)butyl;     -   C₁-C₄-alkoxy-C₁-C₄-alkoxy as alkoxyalkoxy moieties of         C₁-C₄-alkoxy-C₁-C₄-alkoxycarbonyl: C₁-C₄-alkoxy which is         substituted by C₁-C₄-alkoxy as mentioned above, i.e., for         example, methoxymethoxy, ethoxymethoxy, propoxymethoxy,         (1-methylethoxy)methoxy, butoxymethoxy,         (1-methylpropoxy)methoxy, (2-methylpropoxy)methoxy,         (1,1-dimethylethoxy)methoxy, 2-(methoxy)ethoxy,         2-(ethoxy)ethoxy, 2-(propoxy)ethoxy, 2-(1-methylethoxy)ethoxy,         2-(butoxy)ethoxy, 2-(1-methylpropoxy)ethoxy,         2-(2-methylpropoxy)ethoxy, 2-(1,1-dimethylethoxy)ethoxy,         2-(methoxy)propoxy, 2-(ethoxy)propoxy, 2-(propoxy)propoxy,         2-(1-methylethoxy)propoxy, 2-(butoxy)propoxy,         2-(1-methylpropoxy)propoxy, 2-(2-methylpropoxy)propoxy,         2-(1,1-dimethylethoxy)propoxy, 3-(methoxy)propoxy,         3-(ethoxy)propoxy, 3-(propoxy)propoxy,         3-(1-methylethoxy)propoxy, 3-(butoxy)propoxy,         3-(1-methylpropoxy)propoxy, 3-(2-methylpropoxy)propoxy,         3-(1,1-dimethylethoxy)propoxy, 2-(methoxy)butoxy,         2-(ethoxy)butoxy, 2-(propoxy)butoxy, 2-(1-methylethoxy)butoxy,         2-(butoxy)butoxy, 2-(1-methylpropoxy)butoxy,         2-(2-methylpropoxy)butoxy, 2-(1,1-dimethylethoxy)butoxy,         3-(methoxy)butoxy, 3-(ethoxy)butoxy, 3-(propoxy)butoxy,         3-(1-methylethoxy)butoxy, 3-(butoxy)butoxy,         3-(1-methylpropoxy)butoxy, 3-(2-methylpropoxy)butoxy,         3-(1,1-dimethylethoxy)butoxy, 4-(methoxy)butoxy,         4-(ethoxy)butoxy, 4-(propoxy)butoxy, 4-(1-methylethoxy)butoxy,         4-(butoxy)butoxy, 4-(1-methylpropoxy)butoxy,         4-(2-methylpropoxy)butoxy or 4-(1,1-dimethylethoxy)butoxy;     -   C₃-C₆-alkenyl, and the alkenyl moieties of         C₃-C₆-alkenylcarbonyl, C₃-C₆-alkenyloxy,         C₃-C₆-alkenyloxycarbonyl, C₃-C₆-alkenylaminocarbonyl,         N—(C₃-C₆-alkenyl)-N—(C₁-C₆-alkyl)aminocarbonyl,         N—(C₃-C₆-alkenyl)-N—(C₁-C₆-alkoxy)aminocarbonyl: for example         prop-2-en-1-yl, but-1-en-4-yl, 1-methylprop-2-en-1-yl,         2-methylprop-2-en-1-yl, 2-buten-1-yl, 1-penten-3-yl,         1-penten-4-yl, 2-penten-4-yl, 1-methylbut-2-en-1-yl,         2-methylbut-2-en-1-yl, 3-methylbut-2-en-1-yl,         1-methylbut-3-en-1-yl, 2-methylbut-3-en-1-yl,         3-methylbut-3-en-1-yl, 1,1-dimethylprop-2-en-1-yl,         1,2-dimethylprop-2-en-1-yl, 1-ethylprop-2-en-1-yl,         hex-3-en-1-yl, hex-4-en-1-yl, hex-5-en-1-yl,         1-methylpent-3-en-1-yl, 2-methylpent-3-en-1-yl,         3-methylpent-3-en-1-yl, 4-methylpent-3-en-1-yl,         1-methylpent-4-en-1-yl, 2-methylpent-4-en-1-yl,         3-methylpent-4-en-1-yl, 4-methylpent-4-en-1-yl,         1,1-dimethylbut-2-en-1-yl, 1,1-dimethylbut-3-en-1-yl,         1,2-dimethylbut-2-en-1-yl, 1,2-dimethylbut-3-en-1-yl,         1,3-dimethylbut-2-en-1-yl, 1,3-dimethylbut-3-en-1-yl,         2,2-dimethylbut-3-en-1-yl, 2,3-dimethylbut-2-en-1-yl,         2,3-dimethylbut-3-en-1-yl, 3,3-dimethylbut-2-en-1-yl,         1-ethylbut-2-en-1-yl, 1-ethylbut-3-en-1-yl,         2-ethylbut-2-en-1-yl, 2-ethylbut-3-en-1-yl,         1,1,2-trimethylprop-2-en-1-yl, 1-ethyl-1-methylprop-2-en-1-yl or         1-ethyl-2-methylprop-2-en-1-yl;     -   C₂-C₆-alkenyl, and the alkenyl moieties of         C₂-C₆-alkenylcarbonyl, phenyl-C₂-C₆-alkenylcarbonyl and         heterocyclyl-C₂-C₆-alkenylcarbonyl: C₃-C₆-alkenyl as mentioned         above, and also ethenyl;     -   C₂-C₂₀-alkenyl as alkenyl moiety of C₂-C₂₀-alkenylcarbonyl:         C₂-C₆-alkenyl as mentioned above, and also pentadecenyl or         heptadecenyl;     -   C₃-C₆-haloalkenyl: a C₃-C₆-alkenyl radical as mentioned above         which is partially or fully substituted by fluorine, chlorine,         bromine and/or iodine, i.e., for example, 2-chloroallyl,         3-chloroallyl, 2,3-dichloroallyl, 3,3-dichloroallyl,         2,3,3-trichloroallyl, 2,3-dichlorobut-2-phenyl, 2-bromoallyl,         3-bromoallyl, 2,3-dibromoallyl, 3,3-dibromoallyl,         2,3,3-tribromoallyl or 2,3-dibromobut-2-enyl;     -   C₃-C₆-alkynyl, and the alkynyl moieties of         C₃-C₆-alkynylcarbonyl, C₃-C₆-alkynyloxy,         C₃-C₆-alkynyloxycarbonyl, C₃-C₆-alkynylaminocarbonyl,         N—(C₃-C₆-alkynyl)-N—(C₁-C₆-alkyl)aminocarbonyl,         N—(C₃-C₆-alkynyl)-N—(C₁-C₆-alkoxyamino)carbonyl: for example         propargyl, but-1-yn-3-yl, but-1-yn-4-yl, but-2-yn-1-yl,         pent-1-yn-3-yl, pent-1-yn-4-yl, pent-1-yn-5-yl, pent-2-yn-1-yl,         pent-2-yn-4-yl, pent-2-yn-5-yl, 3-methylbut-1-yn-3-yl,         3-methylbut-1-yn-4-yl, hex-1-yn-3-yl, hex-1-yn-4-yl,         hex-1-yn-5-yl, hex-1-yn-6-yl, hex-2-yn-1-yl, hex-2-yn-4-yl,         hex-2-yn-5-yl, hex-2-yn-6-yl, hex-3-yn-1-yl, hex-3-yn-2-yl,         3-methylpent-1-yn-3-yl, 3-methylpent-1-yn-4-yl,         3-methylpent-1-yn-5-yl, 4-methylpent-2-yn-4-yl or         4-methylpent-2-yn-5-yl;     -   C₂-C₆-alkynyl, and the alkynyl moieties of         C₂-C₆-alkynylcarbonyl: C₃-C₆-alkynyl as mentioned above, and         also ethynyl;     -   C₃-C₆-haloalkynyl: a C₃-C₆-alkynyl radical as mentioned above         which is partially or fully substituted by fluorine, chlorine,         bromine and/or iodine, i.e., for example,         1,1-difluoroprop-2-yn-1-yl, 3-iodoprop-2-yn-1-yl,         4-fluorobut-2-yn-1-yl, 4-chlorobut-2-yn-1-yl,         1,1-difluorobut-2-yn-1-yl, 4-iodobut-3-yn-1-yl,         5-fluoropent-3-yn-1-yl, 5-iodopent-4-yn-1-yl,         6-fluorohex-4-yn-1-yl or 6-iodohex-5-yn-1-yl;     -   C₃-C₆-cycloalkyl, and the cycloalkyl moieties of         C₃-C₆-cycloalkylcarbonyl: for example cyclopropyl, cyclobutyl,         cyclopentyl or cyclohexyl;     -   heterocyclyl, and the heterocyclyl moieties of heterocyclyloxy,         heterocyclylcarbonyl, heterocyclyl-C₁-C₆-alkyl,         heterocyclyloxycarbonyl, heterocyclyloxythiocarbonyl,         heterocyclyl-C₂-C₆-alkenylcarbonyl,         heterocyclylcarbonyl-C₁-C₆-alkyl,         N—(C₁-C₆-alkyl)-N-(heterocyclyl)aminocarbonyl,         heterocyclylaminocarbonyl: a saturated, partially saturated or         unsaturated 5- or 6-membered heterocyclic ring which is attached         via carbon and contains one to four identical or different         heteroatoms selected from the following group: oxygen, sulfur         and nitrogen, i.e., for example, 5-membered rings having, for         example, one heteroatom, having two heteroatoms, having three         heteroatoms or having four heteroatoms or, for example,         6-membered rings having, for example, one heteroatom, having two         heteroatoms, having three heteroatoms or having four         heteroatoms, i.e. 5-membered rings having one heteroatom, such         as:         -   tetrahydrofuran-2-yl, tetrahydrofuran-3-yl,             tetrahydrothien-2-yl, tetrahydrothien-3-yl,             tetrahydropyrrol-2-yl, tetrahydropyrrol-3-yl,             2,3-dihydrofuran-2-yl, 2,3-dihydrofuran-3-yl,             2,5-dihydrofuran-2-yl, 2,5-dihydrofuran-3-yl,             4,5-dihydrofuran-2-yl, 4,5-dihydrofuran-3-yl,             2,3-dihydrothien-2-yl, 2,3-dihydrothien-3-yl,             2,5-dihydrothien-2-yl, 2,5-dihydrothien-3-yl,             4,5-dihydrothien-2-yl, 4,5-dihydrothien-3-yl,             2,3-dihydro-1H-pyrrol-2-yl, 2,3-dihydro-1H-pyrrol-3-yl,             2,5-dihydro-1H-pyrrol-2-yl, 2,5-dihydro-1H-pyrrol-3-yl,             4,5-dihydro-1H-pyrrol-2-yl, 4,5-dihydro-1H-pyrrol-3-yl,             3,4-dihydro-2H-pyrrol-2-yl, 3,4-dihydro-2H-pyrrol-3-yl,             3,4-dihydro-5H-pyrrol-2-yl, 3,4-dihydro-5H-pyrrol-3-yl,             2-furyl, 3-furyl, 2-thienyl, 3-thienyl, pyrrol-2-yl or             pyrrol-3-yl;         -   5-membered rings having two heteroatoms such as:             tetrahydropyrazol-3-yl, tetrahydropyrazol-4-yl,             tetrahydroisoxazol-3-yl, tetrahydroisoxazol-4-yl,             tetrahydroisoxazol-5-yl, 1,2-oxathiolan-3-yl,             1,2-oxathiolan-4-yl, 1,2-oxathiolan-5-yl,             tetrahydroisothiazol-3-yl, tetrahydroisothiazol-4-yl,             tetrahydroisothiazol-5-yl, 1,2-dithiolan-3-yl,             1,2-dithiolan-4-yl, tetrahydroimidazol-2-yl,             tetrahydroimidazol-4-yl, tetrahydrooxazol-2-yl,             tetrahydrooxazol-4-yl, tetrahydrooxazol-5-yl,             tetrahydrothiazol-2-yl, tetrahydrothiazol-4-yl,             tetrahydrothiazol-5-yl, 1,3-dioxolan-2-yl,             1,3-dioxolan-4-yl, 1,3-oxathiolan-2-yl, 1,3-oxathiolan-4-yl,             1,3-oxathiolan-5-yl, 1,3-dithiolan-2-yl, 1,3-dithiolan-4-yl,             4,5-dihydro-1H-pyrazol-3-yl, 4,5-dihydro-1H-pyrazol-4-yl,             4,5-dihydro-1H-pyrazol-5-yl, 2,5-dihydro-1H-pyrazol-3-yl,             2,5-dihydro-1H-pyrazol-4-yl, 2,5-dihydro-1H-pyrazol-5-yl,             4,5-dihydroisoxazol-3-yl, 4,5-dihydroisoxazol-4-yl,             4,5-dihydroisoxazol-5-yl, 2,5-dihydroisoxazol-3-yl,             2,5-dihydroisoxazol-4-yl, 2,5-dihydroisoxazol-5-yl,             2,3-dihydroisoxazol-3-yl, 2,3-dihydroisoxazol-4-yl,             2,3-dihydroisoxazol-5-yl, 4,5-dihydroisothiazol-3-yl,             4,5-dihydroisothiazol-4-yl, 4,5-dihydroisothiazol-5-yl,             2,5-dihydroisothiazol-3-yl, 2,5-dihydroisothiazol-4-yl,             2,5-dihydroisothiazol-5-yl, 2,3-dihydroisothiazol-3-yl,             2,3-dihydroisothiazol-4-yl, 2,3-dihydroisothiazol-5-yl,             Δ³-1,2-dithiol-3-yl, Δ³-1,2-dithiol-4-yl,             Δ³-1,2-dithiol-5-yl, 4,5-dihydro-1H-imidazol-2-yl,             4,5-dihydro-1H-imidazol-4-yl, 4,5-dihydro-1H-imidazol-5-yl,             2,5-dihydro-1H-imidazol-2-yl, 2,5-dihydro-1H-imidazol-4-yl,             2,5-dihydro-1H-imidazol-5-yl, 2,3-dihydro-1H-imidazol-2-yl,             2,3-dihydro-1H-imidazol-4-yl, 4,5-dihydrooxazol-2-yl,             4,5-dihydrooxazol-4-yl, 4,5-dihydrooxazol-5-yl,             2,5-dihydrooxazol-2-yl, 2,5-dihydrooxazol-4-yl,             2,5-dihydrooxazol-5-yl, 2,3-dihydrooxazol-2-yl,             2,3-dihydrooxazol-4-yl, 2,3-dihydrooxazol-5-yl,             4,5-dihydrothiazol-2-yl, 4,5-dihydrothiazol-4-yl,             4,5-dihydrothiazol-5-yl, 2,5-dihydrothiazol-2-yl,             2,5-dihydrothiazol-4-yl, 2,5-dihydrothiazol-5-yl,             2,3-dihydrothiazol-2-yl, 2,3-dihydrothiazol-4-yl,             2,3-dihydrothiazol-5-yl, 1,3-dioxol-2-yl, 1,3-dioxol-4-yl,             1,3-dithiol-2-yl, 1,3-dithiol-4-yl, 1,3-oxathiol-2-yl,             1,3-oxathiol-4-yl, 1,3-oxathiol-5-yl, pyrazol-3-yl,             pyrazol-4-yl, isoxazol-3-yl, isoxazol-4-yl, isoxazol-5-yl,             isothiazol-3-yl, isothiazol-4-yl, isothiazol-5-yl,             imidazol-2-yl, imidazol-4-yl, oxazol-2-yl, oxazol-4-yl,             oxazol-5-yl, thiazol-2-yl, thiazol-4-yl or thiazol-5-yl;         -   5-membered rings having three heteroatoms such as:             1,2,3-Δ²-oxadiazolin-4-yl, 1,2,3-Δ²-oxadiazolin-5-yl,             1,2,4-Δ⁴-oxadiazolin-3-yl, 1,2,4-Δ⁴-oxadiazolin-5-yl,             1,2,4-Δ²-oxadiazolin-3-yl, 1,2,4-Δ²-oxadiazolin-5-yl,             1,2,4-Δ³-oxadiazolin-3-yl, 1,2,4-Δ³-oxadiazolin-5-yl,             1,3,4-Δ²-oxadiazolin-2-yl, 1,3,4-Δ²-oxadiazolin-5-yl,             1,3,4-Δ³-oxadiazolin-2-yl, 1,3,4-oxadiazolin-2-yl,             1,2,3-Δ²-thiadiazolin-4-yl, 1,2,3-Δ²-thiadiazolin-5-yl,             1,2,4-Δ⁴-thiadiazolin-3-yl, 1,2,4-Δ⁴-thiadiazolin-5-yl,             1,2,4-Δ³-thiadiazolin-3-yl, 1,2,4-Δ³-thiadiazolin-5-yl,             1,2,4-Δ²-thiadiazolin-3-yl, 1,2,4-Δ²-thiadiazolin-5-yl,             1,3,4-Δ²-thiadiazolin-2-yl, 1,3,4-Δ²-thiadiazolin-5-yl,             1,3,4-Δ³-thiadiazolin-2-yl, 1,3,4-thiadiazolin-2-yl,             1,3,2-dioxathiolan-4-yl, 1,2,3-Δ²-triazolin-4-yl,             1,2,3-Δ²-triazolin-5-yl, 1,2,4-Δ²-triazolin-3-yl,             1,2,4-Δ²-triazolin-5-yl, 1,2,4-Δ³-triazolin-3-yl,             1,2,4-Δ³-triazolin-5-yl, 1,2,4-Δ¹-triazolin-2-yl,             1,2,4-triazolin-3-yl, 3H-1,2,4-dithiazol-5-yl,             2H-1,3,4-dithiazol-5-yl, 2H-1,3,4-oxathiazol-5-yl,             1,2,3-oxadiazol-4-yl, 1,2,3-oxadiazol-5-yl,             1,2,4-oxadiazol-3-yl, 1,2,4,-oxadiazol-5-yl,             1,3,4-oxadiazol-2-yl, 1,2,3-thiadiazol-4-yl,             1,2,3-thiadiazol-5-yl, 1,2,4-thiadiazol-3-yl,             1,2,4-thiadiazol-5-yl, 1,3,4-thiadiazolyl-2-yl,             1,2,3-triazol-4-yl or 1,2,4-triazol-3-yl;         -   5-membered rings having four heteroatoms such as:             tetrazol-5-yl;         -   6-membered rings having one heteroatom such as:             tetrahydropyran-2-yl, tetrahydropyran-3-yl,             tetrahydropyran-4-yl, piperidin-2-yl, piperidin-3-yl,             piperidin-4-yl, tetrahydrothiopyran-2-yl,             tetrahydrothiopyran-3-yl, tetrahydrothiopyran-4-yl,             2H-3,4-dihydropyran-6-yl, 2H-3,4-dihydropyran-5-yl,             2H-3,4-dihydropyran-4-yl, 2H-3,4-dihydropyran-3-yl,             2H-3,4-dihydropyran-2-yl, 2H-3,4-dihydropyran-6-yl,             2H-3,4-dihydrothiopyran-5-yl, 2H-3,4-dihydrothiopyran-4-yl,             2H-3,4-dihydropyran-3-yl, 2H-3,4-dihydropyran-2-yl,             1,2,3,4-tetrahydropyridin-6-yl,             1,2,3,4-tetrahydropyridin-5-yl,             1,2,3,4-tetrahydropyridin-4-yl,             1,2,3,4-tetrahydropyridin-3-yl,             1,2,3,4-tetrahydropyridin-2-yl, 2H-5,6-dihydropyran-2-yl,             2H-5,6-dihydropyran-3-yl, 2H-5,6-dihydropyran-4-yl,             2H-5,6-dihydropyran-5-yl, 2H-5,6-dihydropyran-6-yl,             2H-5,6-dihydrothiopyran-2-yl, 2H-5,6-dihydrothiopyran-3-yl,             2H-5,6-dihydrothiopyran-4-yl, 2H-5,6-dihydrothiopyran-5-yl,             2H-5,6-dihydrothiopyran-6-yl,             1,2,5,6-tetrahydropyridin-2-yl,             1,2,5,6-tetrahydropyridin-3-yl,             1,2,5,6-tetrahydropyridin-4-yl,             1,2,5,6-tetrahydropyridin-5-yl,             1,2,5,6-tetrahydropyridin-6-yl,             2,3,4,5-tetrahydropyridin-2-yl,             2,3,4,5-tetrahydropyridin-3-yl,             2,3,4,5-tetrahydropyridin-4-yl,             2,3,4,5-tetrahydropyridin-5-yl,             2,3,4,5-tetrahydropyridin-6-yl, 4H-pyran-2-yl,             4H-pyran-3-yl, 4H-pyran-4-yl, 4H-thiopyran-2-yl,             4H-thiopyran-3-yl, 4H-thiopyran-4-yl,             1,4-dihydropyridin-2-yl, 1,4-dihydropyridin-3-yl,             1,4-dihydropyridin-4-yl, 2H-pyran-2-yl, 2H-pyran-3-yl,             2H-pyran-4-yl, 2H-pyran-5-yl, 2H-pyran-6-yl,             2H-thiopyran-2-yl, 2H-thiopyran-3-yl, 2H-thiopyran-4-yl,             2H-thiopyran-5-yl, 2H-thiopyran-6-yl,             1,2-dihydropyridin-2-yl, 1,2-dihydropyridin-3-yl,             1,2-dihydropyridin-4-yl, 1,2-dihydropyridin-5-yl,             1,2-dihydropyridin-6-yl, 3,4-dihydropyridin-2-yl,             3,4-dihydropyridin-3-yl, 3,4-dihydropyridin-4-yl,             3,4-dihydropyridin-5-yl, 3,4-dihydropyridin-6-yl,             2,5-dihydropyridin-2-yl, 2,5-dihydropyridin-3-yl,             2,5-dihydropyridin-4-yl, 2,5-dihydropyridin-5-yl,             2,5-dihydropyridin-6-yl, 2,3-dihydropyridin-2-yl,             2,3-dihydropyridin-3-yl, 2,3-dihydropyridin-4-yl,             2,3-dihydropyridin-5-yl, 2,3-dihydropyridin-6-yl,             pyridin-2-yl, pyridin-3-yl or pyridin-4-yl;         -   6-membered rings having two heteroatoms such as:             1,3-dioxan-2-yl, 1,3-dioxan-4-yl, 1,3-dioxan-5-yl,             1,4-dioxan-2-yl, 1,3-dithian-2-yl, 1,3-dithian-4-yl,             1,3-dithian-5-yl, 1,4-dithian-2-yl, 1,3-oxathian-2-yl,             1,3-oxathian-4-yl, 1,3-oxathian-5-yl, 1,3-oxathian-6-yl,             1,4-oxathian-2-yl, 1,4-oxathian-3-yl, 1,2-dithian-3-yl,             1,2-dithian-4-yl, hexahydropyrimidin-2-yl,             hexahydropyrimidin-4-yl, hexahydropyrimidin-5-yl,             hexahydropyrazin-2-yl, hexahydropyridazin-3-yl,             hexahydropyridazin-4-yl, tetrahydro-1,3-oxazin-2-yl,             tetrahydro-1,3-oxazin-4-yl, tetrahydro-1,3-oxazin-5-yl,             tetrahydro-1,3-oxazin-6-yl, tetrahydro-1,3-thiazin-2-yl,             tetrahydro-1,3-thiazin-4-yl, tetrahydro-1,3-thiazin-5-yl,             tetrahydro-1,3-thiazin-6-yl, tetrahydro-1,4-thiazin-2-yl,             tetrahydro-1,4-thiazin-3-yl, tetrahydro-1,4-oxazin-2-yl,             tetrahydro-1,4-oxazin-3-yl, tetrahydro-1,2-oxazin-3-yl,             tetrahydro-1,2-oxazin-4-yl, tetrahydro-1,2-oxazin-5-yl,             tetrahydro-1,2-oxazin-6-yl, 2H-5,6-dihydro-1,2-oxazin-3-yl,             2H-5,6-dihydro-1,2-oxazin-4-yl,             2H-5,6-dihydro-1,2-oxazin-5-yl,             2H-5,6-dihydro-1,2-oxazin-6-yl,             2H-5,6-dihydro-1,2-thiazin-3-yl,             2H-5,6-dihydro-1,2-thiazin-4-yl,             2H-5,6-dihydro-1,2-thiazin-5-yl,             2H-5,6-dihydro-1,2-thiazin-6-yl,             4H-5,6-dihydro-1,2-oxazin-3-yl,             4H-5,6-dihydro-1,2-oxazin-4-yl,             4H-5,6-dihydro-1,2-oxazin-5-yl,             4H-5,6-dihydro-1,2-oxazin-6-yl,             4H-5,6-dihydro-1,2-thiazin-3-yl,             4H-5,6-dihydro-1,2-thiazin-4-yl,             4H-5,6-dihydro-1,2-thiazin-5-yl,             4H-5,6-dihydro-1,2-thiazin-6-yl,             2H-3,6-dihydro-1,2-oxazin-3-yl,             2H-3,6-dihydro-1,2-oxazin-4-yl,             2H-3,6-dihydro-1,2-oxazin-5-yl,             2H-3,6-dihydro-1,2-oxazin-6-yl,             2H-3,6-dihydro-1,2-thiazin-3-yl,             2H-3,6-dihydro-1,2-thiazin-4-yl,             2H-3,6-dihydro-1,2-thiazin-5-yl,             2H-3,6-dihydro-1,2-thiazin-6-yl,             2H-3,4-dihydro-1,2-oxazin-3-yl,             2H-3,4-dihydro-1,2-oxazin-4-yl,             2H-3,4-dihydro-1,2-oxazin-5-yl,             2H-3,4-dihydro-1,2-oxazin-6-yl,             2H-3,4-dihydro-1,2-thiazin-3-yl,             2H-3,4-dihydro-1,2-thiazin-4-yl,             2H-3,4-dihydro-1,2-thiazin-5-yl,             2H-3,4-dihydro-1,2-thiazin-6-yl,             2,3,4,5-tetrahydropyridazin-3-yl,             2,3,4,5-tetrahydropyridazin-4-yl,             2,3,4,5-tetrahydropyridazin-5-yl,             2,3,4,5-tetrahydropyridazin-6-yl,             3,4,5,6-tetrahydropyridazin-3-yl,             3,4,5,6-tetrahydropyridazin-4-yl,             1,2,5,6-tetrahydropyridazin-3-yl,             1,2,5,6-tetrahydropyridazin-4-yl,             1,2,5,6-tetrahydropyridazin-5-yl,             1,2,5,6-tetrahydropyridazin-6-yl,             1,2,3,6-tetrahydropyridazin-3-yl,             1,2,3,6-tetrahydropyridazin-4-yl,             4H-5,6-dihydro-1,3-oxazin-2-yl,             4H-5,6-dihydro-1,3-oxazin-4-yl,             4H-5,6-dihydro-1,3-oxazin-5-yl,             4H-5,6-dihydro-1,3-oxazin-6-yl,             4H-5,6-dihydro-1,3-thiazin-2-yl,             4H-5,6-dihydro-1,3-thiazin-4-yl,             4H-5,6-dihydro-1,3-thiazin-5-yl,             4H-5,6-dihydro-1,3-thiazin-6-yl,             3,4,5,6-tetrahydropyrimidin-2-yl,             3,4,5,6-tetrahydropyrimidin-4-yl,             3,4,5,6-tetrahydropyrimidin-5-yl,             3,4,5,6-tetrahydropyrimidin-6-yl,             1,2,3,4-tetrahydropyrazin-2-yl,             1,2,3,4-tetrahydropyrazin-5-yl,             1,2,3,4-tetrahydropyrimidin-2-yl,             1,2,3,4-tetrahydropyrimidin-4-yl,             1,2,3,4-tetrahydropyrimidin-5-yl,             1,2,3,4-tetrahydropyrimidin-6-yl,             2,3-dihydro-1,4-thiazin-2-yl, 2,3-dihydro-1,4-thiazin-3-yl,             2,3-dihydro-1,4-thiazin-5-yl, 2,3-dihydro-1,4-thiazin-6-yl,             2H-1,2-oxazin-3-yl, 2H-1,2-oxazin-4-yl, 2H-1,2-oxazin-5-yl,             2H-1,2-oxazin-6-yl, 2H-1,2-thiazin-3-yl,             2H-1,2-thiazin-4-yl, 2H-1,2-thiazin-5-yl,             2H-1,2-thiazin-6-yl, 4H-1,2-oxazin-3-yl, 4H-1,2-oxazin-4-yl,             4H-1,2-oxazin-5-yl, 4H-1,2-oxazin-6-yl, 4H-1,2-thiazin-3-yl,             4H-1,2-thiazin-4-yl, 4H-1,2-thiazin-5-yl,             4H-1,2-thiazin-6-yl, 6H-1,2-oxazin-3-yl, 6H-1,2-oxazin-4-yl,             6H-1,2-oxazin-5-yl, 6H-1,2-oxazin-6-yl, 6H-1,2-thiazin-3-yl,             6H-1,2-thiazin-4-yl, 6H-1,2-thiazin-5-yl,             6H-1,2-thiazin-6-yl, 2H-1,3-oxazin-2-yl, 2H-1,3-oxazin-4-yl,             2H-1,3-oxazin-5-yl, 2H-1,3-oxazin-6-yl, 2H-1,3-thiazin-2-yl,             2H-1,3-thiazin-4-yl, 2H-1,3-thiazin-5-yl,             2H-1,3-thiazin-6-yl, 4H-1,3-oxazin-2-yl, 4H-1,3-oxazin-4-yl,             4H-1,3-oxazin-5-yl, 4H-1,3-oxazin-6-yl, 4H-1,3-thiazin-2-yl,             4H-1,3-thiazin-4-yl, 4H-1,3-thiazin-5-yl,             4H-1,3-thiazin-6-yl, 6H-1,3-oxazin-2-yl, 6H-1,3-oxazin-4-yl,             6H-1,3-oxazin-5-yl, 6H-1,3-oxazin-6-yl, 6H-1,3-thiazin-2-yl,             6H-1,3-oxazin-4-yl, 6H-1,3-oxazin-5-yl, 6H-1,3-thiazin-6-yl,             2H-1,4-oxazin-2-yl, 2H-1,4-oxazin-3-yl, 2H-1,4-oxazin-5-yl,             2H-1,4-oxazin-6-yl, 2H-1,4-thiazin-2-yl,             2H-1,4-thiazin-3-yl, 2H-1,4-thiazin-5-yl,             2H-1,4-thiazin-6-yl, 4H-1,4-oxazin-2-yl, 4H-1,4-oxazin-3-yl,             4H-1,4-thiazin-2-yl, 4H-1,4-thiazin-3-yl,             1,4-dihydropyridazin-3-yl, 1,4-dihydropyridazin-4-yl,             1,4-dihydropyridazin-5-yl, 1,4-dihydropyridazin-6-yl,             1,4-dihydropyrazin-2-yl, 1,2-dihydropyrazin-2-yl,             1,2-dihydropyrazin-3-yl, 1,2-dihydropyrazin-5-yl,             1,2-dihydropyrazin-6-yl, 1,4-dihydropyrimidin-2-yl,             1,4-dihydropyrimidin-4-yl, 1,4-dihydropyrimidin-5-yl,             1,4-dihydropyrimidin-6-yl, 3,4-dihydropyrimidin-2-yl,             3,4-dihydropyrimidin-4-yl, 3,4-dihydropyrimidin-5-yl or             3,4-dihydropyrimidin-6-yl, pyridazin-3-yl, pyridazin-4-yl,             pyrimidin-2-yl, pyrimidin-4-yl, pyrimidin-5-yl or             pyrazin-2-yl;         -   6-membered rings having three heteroatoms such as:             1,3,5-triazin-2-yl, 1,2,4-triazin-3-yl, 1,2,4-triazin-5-yl,             1,2,4-triazin-6-yl;         -   6-membered rings having four heteroatoms such as:             1,2,4,5-tetrazin-3-yl;         -   where, if appropriate, the sulfur of the above-mentioned             heterocycles may be oxidized to S═O or S(═O)₂         -   and where a bicyclic ring system may be formed with a             fused-on phenyl ring or with a C₃-C₆-carbocycle or with a             further 5- to 6-membered heterocycle.     -   N-bonded heterocyclyl: a saturated, partially saturated or         unsaturated 5- or 6-membered heterocyclic ring which is attached         via nitrogen and contains at least one nitrogen and, if         appropriate, one to three identical or different heteroatoms         selected from the following group: oxygen, sulfur and nitrogen,         i.e., for example,         -   N-bonded 5-membered rings such as: tetrahydropyrrol-1-yl,             2,3-dihydro-1H-pyrrol-1-yl, 2,5-dihydro-1H-pyrrol-1-yl,             pyrrol-1-yl, tetrahydropyrazol-1-yl,             tetrahydroisoxazol-2-yl, tetrahydroisothiazol-2-yl,             tetrahydroimidazol-1-yl, tetrahydrooxazol-3-yl,             tetrahydrothiazol-3-yl, 4,5-dihydro-1H-pyrazol-1-yl,             2,5-dihydro-1H-pyrazol-1-yl, 2,3-dihydro-1H-pyrazol-1-yl,             2,5-dihydroisoxazol-2-yl, 2,3-dihydroisoxazol-2-yl,             2,5-dihydroisothiazol-2-yl, 2,3-dihydroisoxazol-2-yl,             4,5-dihydro-1H-imidazol-1-yl, 2,5-dihydro-1H-imidazol-1-yl,             2,3-dihydro-1H-imidazol-1-yl, 2,3-dihydrooxazol-3-yl,             2,3-dihydrothiazol-3-yl, pyrazol-1-yl, imidazol-1-yl,             1,2,4-Δ⁴-oxadiazolin-2-yl, 1,2,4-Δ²-oxadiazolin-4-yl,             1,2,4-Δ³-oxadiazolin-2-yl, 1,3,4-Δ²-oxadiazolin-4-yl,             1,2,4-Δ⁵-thiadiazolin-2-yl, 1,2,4-Δ³-thiadiazolin-2-yl,             1,2,4-Δ²-thiadiazolin-4-yl, 1,3,4-Δ²-thiadiazolin-4-yl,             1,2,3-Δ²-triazolin-1-yl, 1,2,4-Δ²-triazolin-1-yl,             1,2,4-Δ²-triazolin-4-yl, 1,2,4-Δ³-triazolin-1-yl,             1,2,4-Δ¹-triazolin-4-yl, 1,2,3-triazol-1-yl,             1,2,4-triazol-1-yl, tetrazol-1-yl;         -   and also N-bonded 6-membered rings such as: piperidin-1-yl,             1,2,3,4-tetrahydropyridin-1-yl,             1,2,5,6-tetrahydropyridin-1-yl, 1,4-dihydropyridin-1-yl,             1,2-dihydropyridin-1-yl, hexahydropyrimidin-1-yl,             hexahydropyrazin-1-yl, hexahydropyridazin-1-yl,             tetrahydro-1,3-oxazin-3-yl, tetrahydro-1,3-thiazin-3-yl,             tetrahydro-1,4-thiazin-4-yl, tetrahydro-1,4-oxazin-4-yl,             tetrahydro-1,2-oxazin-2-yl, 2H-5,6-dihydro-1,2-oxazin-2-yl,             2H-5,6-dihydro-1,2-thiazin-2-yl,             2H-3,6-dihydro-1,2-oxazin-2-yl,             2H-3,6-dihydro-1,2-thiazin-2-yl,             2H-3,4-dihydro-1,2-oxazin-2-yl,             2H-3,4-dihydro-1,2-thiazin-2-yl,             2,3,4,5-tetrahydropyridazin-2-yl,             1,2,5,6-tetrahydropyridazin-1-yl,             1,2,5,6-tetrahydropyridazin-2-yl,             1,2,3,6-tetrahydropyridazin-1-yl,             3,4,5,6-tetrahydropyrimidin-3-yl,             1,2,3,4-tetrahydropyrazin-1-yl,             1,2,3,4-tetrahydropyrimidin-1-yl,             1,2,3,4-tetrahydropyrimidin-3-yl,             2,3-dihydro-1,4-thiazin-4-yl, 2H-1,2-oxazin-2-yl,             2H-1,2-thiazin-2-yl, 4H-1,4-oxazin-4-yl,             4H-1,4-thiazin-4-yl, 1,4-dihydropyridazin-1-yl,             1,4-dihydropyrazin-1-yl, 1,2-dihydropyrazin-1-yl,             1,4-dihydropyrimidin-1-yl or 3,4-dihydropyrimidin-3-yl;         -   and also N-bonded cyclic imides such as:         -   phthalimide, tetrahydrophthalimide, succinimide, maleimide,             glutarimide, 5-oxotriazolin-1-yl,             5-oxo-1,3,4-oxadiazolin-4-yl or             2,4-dioxo-(1H,3H)-pyrimidin-3-yl;         -   where a bicyclic ring system may be formed with a fused-on             phenyl ring or with a C₃-C₆-carbocycle or a further 5- to             6-membered heterocycle.

All phenyl rings, heterocyclyl or N-heterocyclyl radicals and all phenyl components in phenoxy, phenyl-C₁-C₆-alkyl, phenylcarbonyl-C₁-C₆-alkyl, phenylcarbonyl, phenylalkenylcarbonyl, phenoxycarbonyl, phenyloxythiocarbonyl, phenylaminocarbonyl and N—(C₁-C₆-alkyl)-N-phenylaminocarbonyl or heterocyclyl components in heterocyclyloxy, heterocyclyl-C₁-C₆-alkyl, heterocyclylcarbonyl-C₁-C₆-alkyl, heterocyclylcarbonyl, heterocyclyloxythiocarbonyl, heterocyclylalkenylcarbonyl, heterocyclyloxycarbonyl, heterocyclylaminocarbonyl and N—(C₁-C₆-alkyl)-N-heterocyclylaminocarbonyl are, unless stated otherwise, preferably unsubstituted, or they carry one to three halogen atoms and/or one nitro group, one cyano radical and/or one or two methyl, trifluoromethyl, methoxy or trifluoromethoxy substitutents.

Furthermore, the expression “Y together with the two carbons to which it is attached forms a saturated, partially saturated or unsaturated heterocycle which contains one to three identical or different heteroatoms selected from the following group: oxygen, sulfur and nitrogen” denotes, for example, 5-membered rings having one heteroatom such as:

tetrahydrofurandiyl, tetrahydrothienediyl, tetrahydropyrrolediyl, dihydrofurandiyl, dihydrothienediyl, dihydropyrrolediyl, furandiyl, thienediyl or pyrrolediyl;

or 5-membered rings having two heteroatoms such as:

tetrahydropyrazolediyl, tetrahydroisoxazolediyl, 1,2-oxathiolanediyl, tetrahydroisothiazolediyl, 1,2-dithiolanediyl, tetrahydroimidazolediyl, tetrahydrooxazolediyl, tetrahydrothiazolediyl, 1,3-dioxolanediyl, 1,3-oxathiolanediyl, dihydropyrazolediyl, dihydroisoxazolediyl, dihydroisothiazolediyl, 1,2-dithiolediyl, dihydroimidazolediyl, dihydrooxazolediyl, dihydrothiazolediyl, dioxolediyl, oxathiolediyl, pyrazolediyl, isoxazolediyl, isothiazolediyl, imidazolediyl, oxazolediyl or thiazolediyl;

or 5-membered rings having three heteroatoms such as:

1,2,3-oxadiazolinediyl, 1,2,3-thiadiazolinediyl, 1,2,3-triazolinediyl, 1,2,3-oxadiazolediyl, 1,2,3-thiadiazolediyl or 1,2,3-triazolediyl;

or 6-membered rings having one heteroatom such as:

tetrahydropyrandiyl, piperidinediyl, tetrahydrothiopyrandiyl, dihydropyrandiyl, dihydrothiopyrandiyl, tetrahydropyridinediyl, pyrandiyl, thiopyrandiyl, dihydropyrinediyl or pyridinediyl;

or 6-membered rings having two heteroatoms such as:

1,3-dioxanediyl, 1,4-dioxanediyl, 1,3-dithianediyl, 1,4-dithianediyl, 1,3-oxathianediyl, 1,4-oxathianediyl, 1,2-dithianediyl, hexahydropyrimidinediyl, hexahydropyrazinediyl, hexahydropyridazinediyl, tetrahydro-1,3-oxazinediyl, tetrahydro-1,3-thiazinediyl, tetrahydro-1,4-oxazinediyl, tetrahydro-1,2-oxazinediyl, dihydro-1,2-oxazinediyl, dihydro-1,2-thiazinediyl, tetrahydropyridazinediyl, dihydro-1,3-oxazinediyl, dihydro-1,3-oxazinediyl, dihydro-1,3-thiazinediyl, tetrahydropyrimidinediyl, tetrahydropyrazinediyl, dihydro-1,4-thiazinediyl, dihydro-1,4-oxazinediyl, dihydro-1,4-dioxinediyl, dihydro-1,4-dithiinediyl, 1,2-oxazinediyl, 1,2-thiazinediyl, 1,3-oxazinediyl, 1,3-thiazinediyl, 1,4-oxazinediyl, 1,4-thiazinediyl, dihydropyridazinediyl, dihydropyrazinediyl, dihydropyrimidinediyl, pyridazinediyl, pyrimidinediyl or pyrazinediyl;

or 6-membered rings having 3 heteroatoms such as:

1,2,4-triazinediyl;

where, if appropriate, the sulfur of the abovementioned heterocycles may be oxidized to S═O or S(═O)₂;

and where the moiety is fused to the skeleton via two adjacent carbon atoms.

The compounds of the formula I according to the invention where R⁹=IIa are referred to as compounds of the formula Ia, and compounds of the formula I where R⁹=IIb are referred to as Ib.

Preference is given to the compounds of the formula I, where

-   R¹¹ is hydrogen, C₁-C₆-alkyl, C₁-C₆-haloalkyl, hydroxyl,     C₁-C₆-alkoxy or C₁-C₆-haloalkoxy;

Preference is likewise given to the compounds of the formula Ia.

With respect to the use of the compounds of the formula I according to the invention as herbicides, the variables preferably have the following meanings, in each case alone or in combination:

-   X is oxygen, sulfur, S═O, S(═O)₂, CR⁶R⁷, NR⁸ or a bond; -   Y together with the two carbons to which it is attached forms a     saturated, partially saturated or unsaturated 5- or 6-membered     heterocycle which contains one or two identical or different     heteroatoms selected from the following group: oxygen, sulfur or     nitrogen; -   R¹, R² are hydrogen or C₁-C₆-alkyl; -   R³ is halogen, C₁-C₆-alkyl or C₁-C₆-alkoxy; -   R⁴ is nitro, halogen, cyano, C₁-C₆-alkyl, C₁-C₆-haloalkyl,     C₁-C₆-alkoxy, C₁-C₆-haloalkoxy, C₁-C₆-alkylthio,     C₁-C₆-haloalkylthio, C₁-C₆-alkylsulfinyl, C₁-C₆-haloalkylsulfinyl,     C₁-C₆-alkylsulfonyl, C₁-C₆-haloalkylsulfonyl, aminosulfonyl,     N—(C₁-C₆-alkyl)aminosulfonyl, N,N-di(C₁-C₆-alkyl)aminosulfonyl,     N—(C₁-C₆-alkylsulfonyl)amino, N—(C₁-C₆-haloalkylsulfonyl)amino,     N—(C₁-C₆-alkyl)-N—(C₁-C₆-alkylsulfonyl)amino or     N—(C₁-C₆-alkyl)-N—(C₁-C₆-haloalkylsulfonyl)amino;     -   in particular nitro, halogen, C₁-C₆-alkyl, C₁-C₆-haloalkyl,         C₁-C₆-alkoxy, C₁-C₆-haloalkoxy, C₁-C₆-alkylthio,         C₁-C₆-haloalkylthio, C₁-C₆-alkylsulfonyl or         C₁-C₆-haloalkylsulfonyl; -   R⁵ is hydrogen; -   R⁶, R⁷ are hydrogen or C₁-C₆-alkyl; -   R⁸ is C₁-C₆-alkyl, C₁-C₆-alkylcarbonyl or C₁-C₆-alkylsulfonyl; -   l is 0, 1 or 2; -   R⁹ is a radical IIa     where -   R¹⁰ is hydroxyl, mercapto, halogen, OR¹³, SR¹³, SO₂R¹⁴ or N-bonded     heterocyclyl, where the heterocyclyl radical may be partially or     fully halogenated and/or may carry one to three of the following     radicals:     -   nitro, cyano, C₁-C₄-alkyl, C₁-C₄-haloalkyl, C₁-C₄-alkoxy or         C₁-C₄-haloalkoxy; -   R¹¹ is hydrogen, C₁-C₆-alkyl, C₁-C₆-haloalkyl or C₃-C₆-cycloalkyl; -   R¹² is hydrogen, C₁-C₆-alkyl or C₁-C₆-haloalkyl; -   R¹³ is C₁-C₆-alkyl, C₃-C₆-alkenyl, C₃-C₆-haloalkenyl, C₃-C₆-alkynyl,     C₁-C₆-alkylcarbonyl, C₂-C₆-alkenylcarbonyl,     C₃-C₆-cycloalkylcarbonyl, C₁-C₆-alkoxycarbonyl,     C₃-C₆-alkenyloxycarbonyl, C₃-C₆-alkynyloxycarbonyl,     C₁-C₆-alkylthiocarbonyl, C₁-C₆-alkylaminocarbonyl,     C₃-C₆-alkenylaminocarbonyl, C₃-C₆-alkynylaminocarbonyl,     N,N-di(C₁-C₆-alkyl)aminocarbonyl,     N—(C₃-C₆-alkenyl)-N—(C₁-C₆-alkyl)aminocarbonyl,     N—(C₃-C₆-alkynyl)-N—(C₁-C₆-alkyl)aminocarbonyl,     N—(C₁-C₆-alkoxy)-N—(C₁-C₆-alkyl) aminocarbonyl,     N—(C₃-C₆-alkenyl)-N—(C₁-C₆-alkoxy)aminocarbonyl     N—(C₃-C₆-alkynyl)-N—(C₁-C₆-alkoxy)aminocarbonyl,     di(C₁-C₆-alkyl)aminothiocarbonyl, C₁-C₆-alkylcarbonyl-C₁-C₆-alkyl,     C₁-C₆-alkoxyimino-C₁-C₆-alkyl, N—(C₁-C₆-alkylamino)imino-C₁-C₆-alkyl     or N,N-di(C₁-C₆-alkylamino)imino-C₁-C₆-alkyl, where the     abovementioned alkyl, cycloalkyl and alkoxy radicals may be     partially or fully halogenated and/or may carry one to three of the     following groups:     -   cyano, C₁-C₄-alkoxy, C₁-C₄-alkylthio, C₁-C₄-alkylcarbonyl,         C₁-C₄-alkoxycarbonyl, hydroxycarbonyl,         di(C₁-C₄-alkyl)aminocarbonyl, C₁-C₄-alkylcarbonyloxy or         C₃-C₆-cycloalkyl;     -   is phenyl, heterocyclyl, phenyl-C₁-C₆-alkyl,         heterocyclyl-C₁-C₆-alkyl, phenylcarbonyl-C₁-C₆-alkyl,         heterocyclylcarbonyl-C₁-C₆-alkyl, phenylcarbonyl,         heterocyclylcarbonyl, phenoxycarbonyl, phenyloxythiocarbonyl,         heterocyclyloxycarbonyl, heterocyclyloxythiocarbonyl,         phenyl-C₂-C₆-alkenylcarbonyl or         heterocyclyl-C₂-C₆-alkenylcarbonyl, where the phenyl and the         heterocyclyl radical of the 14 lastmentioned substitutents may         be partially or fully halogenated and/or may carry one to three         of the following radicals:     -   nitro, cyano, C₁-C₄-alkyl, C₁-C₄-haloalkyl, C₁-C₄-alkoxy,         C₁-C₄-haloalkoxy, heterocyclyl or N-bonded heterocyclyl, where         the two lastmentioned substitutents for their part may be         partially or fully halogenated and/or may carry one to three of         the following radicals: nitro, cyano, C₁-C₄-alkyl,         C₁-C₄-haloalkyl, C₁-C₄-alkoxy or C₁-C₄-haloalkoxy; -   R¹⁴ is C₁-C₆-alkyl, C₃-C₆-alkenyl, C₃-C₆-haloalkenyl,     C₃-C₆-cycloalkyl, C₁-C₆-alkoxy or di(C₁-C₆-haloalkyl)amino, where     the abovementioned alkyl, cycloalkyl and alkoxy radicals may be     partially or fully halogenated and/or may carry one to three of the     following groups:     -   cyano, C₁-C₄-alkoxy, C₁-C₄-alkylthio, C₁-C₄-alkylcarbonyl,         C₁-C₄-alkoxycarbonyl, hydroxycarbonyl,         di(C₁-C₄-alkyl)aminocarbonyl, C₁-C₄-alkylcarbonyloxy or         C₃-C₆-cycloalkyl;     -   is phenyl, heterocyclyl, phenyl-C₁-C₆-alkyl,         heterocyclyl-C₁-C₆-alkyl, phenoxy, heterocyclyloxy, where the         phenyl and the heterocyclyl radical of the lastmentioned         substitutents may be partially or fully halogenated and/or may         carry one to three of the following radicals:     -   nitro, cyano, C₁-C₄-alkyl, C₁-C₄-haloalkyl, C₁-C₄-alkoxy or         C₁-C₄-haloalkoxy.

Particular preference is given to compounds of the formula I where the variables have the following meanings, either alone or in combination:

-   X is oxygen, sulfur, S═O, S(═O)₂, CR⁶R⁷ or a bond; -   Y together with the two carbons to which it is attached forms the     following heterocycles:     -   (in the embodiments of the heterocycles below, the upper         undulating line represents in each case the link to the         hydrocarbon which carries the radicals R¹ and R², and the lower         undulating line represents the link to the meta-carbon of the         benzoyl moiety).         where the sulfur of the abovementioned heterocycles may be         oxidized to S═O or S(═O)₂;         in particular, Y together with the two carbons to which it is         attached forms the following heterocycles: -   R¹, R² are hydrogen; -   R³ is C₁-C₆-alkyl, such as methyl, ethyl or n-propyl; in particular     methyl; -   R⁴ is nitro, halogen, C₁-C₆-alkyl, C₁-C₆-haloalkyl, C₁-C₆-alkoxy,     C₁-C₆-alkylthio or C₁-C₆-alkylsulfonyl; in particular nitro,     halogen, such as fluorine, chlorine or bromine, C₁-C₆-haloalkyl such     as trifluoromethyl, C₁-C₆-alkylthio, such as methylthio or     ethylthio, or C₁-C₆-alkylsulfonyl, such as methylsulfonyl or     ethylsulfonyl;     -   particularly preferably nitro, chlorine, trifluoromethyl,         methylthio or methylsulfonyl; -   R⁵ is hydrogen; -   R⁶, R⁷ are hydrogen or C₁-C₆-alkyl, such as methyl or ethyl;     -   in particular hydrogen or methyl; -   l is 0, 1 or 2;     -   in particular 0 or 1; -   R⁹ is a radical IIa     where -   R¹⁰ is hydroxyl; -   R¹¹ is C₁-C₆-alkyl, such as methyl, ethyl, n-propyl, 1-methylethyl,     n-butyl, 2-methylpropyl or 1,1-dimethylethyl or cyclopropyl;     -   in particular methyl or ethyl;     -   likewise particularly preferred cyclopropyl; -   R¹² is hydrogen or C₁-C₆-alkyl, such as methyl, ethyl, n-propyl or     1-methylethyl;     -   in particular hydrogen or methyl.

Very particular preference is given to the compounds 1a where

-   X is oxygen, sulfur, S(═O)₂, CH₂ or a bond; -   Y together with the two carbons to which it is attached forms the     following heterocycles: -   R¹, R² are hydrogen; -   R³ is C₁-C₄-alkyl; -   R⁴ is nitro, halogen, C₁-C₆-alkyl, C₁-C₆-haloalkyl, C₁-C₆-alkoxy,     C₁-C₆-alkylthio or C₁-C₆-alkylsulfonyl; -   R⁵ is hydrogen or C₁-C₆-alkyl; -   l is 0, 1 or 2; -   R⁹ is a radical IIa; -   R¹⁰ is hydroxyl; -   R¹¹ is hydrogen, C₁-C₆-alkyl or cyclopropyl;     -   in particular C₁-C₆-alkyl; -   R¹² is hydrogen, C₁-C₆-alkyl or C₁-C₆-haloalkyl.

Very particular preference is also given to the compounds Ia where X is oxygen, sulfur or a bond.

Very particular preference is also given to the compounds 1a where

-   Y together with the two carbons to which it is attached forms a     heterocycle selected from the following group: dihydropyrazolediyl,     dihydroisoxazolediyl, pyrazolediyl, isoxazolediyl or pyrimidinediyl.

Most preferably, Y together with the two carbons to which it is attached forms the following heterocycles:

Very particular preference is also given to the compounds of the formula I where

-   R¹, R² are hydrogen; -   R³ is C₁-C₆-alkyl; -   R⁴ is nitro, halogen, C₁-C₆-alkyl, C₁-C₆-haloalkyl, C₁-C₆-alkoxy,     C₁-C₆-alkylthio or C₁-C₆-alkylsulfonyl;     -   in particular halogen, C₁-C₆-alkoxy, C₁-C₆-alkylthio or         C₁-C₆-alkylsulfonyl; -   R⁵ is hydrogen; -   l is 0 oder 1.

Very particular preference is also given to the compounds of the formula I where

-   R¹⁰ is hydroxyl or phenylcarbonyloxy which may be unsubstituted or     partially or fully halogenated and/or may carry one to three of the     following radicals: nitro, cyano, C₁-C₄-alkyl, C₁-C₄-haloalkyl,     C₁-C₄-alkoxy or C₁-C₄-haloalkoxy;     -   in particular hydroxyl; -   R¹¹ is C₁-C₆-alkyl or C₃-C₆-cycloalkyl;     -   in particular C₁-C₆-alkyl or     -   also in particular cyclopropyl; -   R¹² is hydrogen or C₁-C₆-alkyl;     -   in particular hydrogen.

Very particular preference is also given to the compounds of the formula Ia1 (≡Ia where R¹, R², R⁵ and R¹²=H, l=0, meaning of the heterocycle according to structural formula), most particularly to compounds Ia1.n where the variables X, R⁴, R¹⁰ and R¹¹ are as defined in Table 1.

The radical definitions of R¹ to R¹², X, Y and l given above and the meaning of the fused heterocycle are of particular importance for the compounds according to the invention, not only in combination with one another, but also taken on their own. (For reasons of clarity, in the formulae Ia1, Ia2 . . . , the meaning of the fused heterocycle is in each case as given in the corresponding structural formula.) TABLE 1 Ia1

n X R⁴ R¹⁰ R¹¹   1 bond F OH CH₃   2 bond Cl OH CH₃   3 bond Br OH CH₃   4 bond NO₂ OH CH₃   5 bond SCH₃ OH CH₃   6 bond SO₂CH₃ OH CH₃   7 bond SO₂CH₂CH₃ OH CH₃   8 bond CH₃ OH CH₃   9 bond CF₃ OH CH₃  10 bond OCHF₂ OH CH₃  11 CH₂ F OH CH₃  12 CH₂ Cl OH CH₃  13 CH₂ Br OH CH₃  14 CH₂ NO₂ OH CH₃  15 CH₂ SCH₃ OH CH₃  16 CH₂ SO₂CH₃ OH CH₃  17 CH₂ SO₂CH₂CH₃ OH CH₃  18 CH₂ CH₃ OH CH₃  19 CH₂ CF₃ OH CH₃  20 CH₂ OCHF₂ OH CH₃  21 O F OH CH₃  22 O Cl OH CH₃  23 O Br OH CH₃  24 O NO₂ OH CH₃  25 O SCH₃ OH CH₃  26 O SO₂CH₃ OH CH₃  27 O SO₂CH₂CH₃ OH CH₃  28 O CH₃ OH CH₃  29 O CF₃ OH CH₃  30 O OCHF₂ OH CH₃  31 S F OH CH₃  32 S Cl OH CH₃  33 S Br OH CH₃  34 S NO₂ OH CH₃  35 S SCH₃ OH CH₃  36 S SO₂CH₃ OH CH₃  37 S SO₂CH₂CH₃ OH CH₃  38 S CH₃ OH CH₃  39 S CF₃ OH CH₃  40 S OCHF₂ OH CH₃  41 SO₂ F OH CH₃  42 SO₂ Cl OH CH₃  43 SO₂ Br OH CH₃  44 SO₂ NO₂ OH CH₃  45 SO₂ SCH₃ OH CH₃  46 SO₂ SO₂CH₃ OH CH₃  47 SO₂ SO₂CH₂CH₃ OH CH₃  48 SO₂ CH₃ OH CH₃  49 SO₂ CF₃ OH CH₃  50 SO₂ OCHF₂ OH CH₃  51 bond F OH CH₂CH₃  52 bond Cl OH CH₂CH₃  53 bond Br OH CH₂CH₃  54 bond NO₂ OH CH₂CH₃  55 bond SCH₃ OH CH₂CH₃  56 bond SO₂CH₃ OH CH₂CH₃  57 bond SO₂CH₂CH₃ OH CH₂CH₃  58 bond CH₃ OH CH₂CH₃  59 bond CF₃ OH CH₂CH₃  60 bond OCHF₂ OH CH₂CH₃  61 CH₂ F OH CH₂CH₃  62 CH₂ Cl OH CH₂CH₃  63 CH₂ Br OH CH₂CH₃  64 CH₂ NO₂ OH CH₂CH₃  65 CH₂ SCH₃ OH CH₂CH₃  66 CH₂ SO₂CH₃ OH CH₂CH₃  67 CH₂ SO₂CH₂CH₃ OH CH₂CH₃  68 CH₂ CH₃ OH CH₂CH₃  69 CH₂ CF₃ OH CH₂CH₃  70 CH₂ OCHF₂ OH CH₂CH₃  71 O F OH CH₂CH₃  72 O Cl OH CH₂CH₃  73 O Br OH CH₂CH₃  74 O NO₂ OH CH₂CH₃  75 O SCH₃ OH CH₂CH₃  76 O SO₂CH₃ OH CH₂CH₃  77 O SO₂CH₂CH₃ OH CH₂CH₃  78 O CH₃ OH CH₂CH₃  79 O CF₃ OH CH₂CH₃  80 O OCHF₂ OH CH₂CH₃  81 S F OH CH₂CH₃  82 S Cl OH CH₂CH₃  83 S Br OH CH₂CH₃  84 S NO₂ OH CH₂CH₃  85 S SCH₃ OH CH₂CH₃  86 S SO₂CH₃ OH CH₂CH₃  87 S SO₂CH₂CH₃ OH CH₂CH₃  88 S CH₃ OH CH₂CH₃  89 S CF₃ OH CH₂CH₃  90 S OCHF₂ OH CH₂CH₃  91 SO₂ F OH CH₂CH₃  92 SO₂ Cl OH CH₂CH₃  93 SO₂ Br OH CH₂CH₃  94 SO₂ NO₂ OH CH₂CH₃  95 SO₂ SCH₃ OH CH₂CH₃  96 SO₂ SO₂CH₃ OH CH₂CH₃  97 SO₂ SO₂CH₂CH₃ OH CH₂CH₃  98 SO₂ CH₃ OH CH₂CH₃  99 SO₂ CF₃ OH CH₂CH₃  100 SO₂ OCHF₂ OH CH₂CH₃  101 bond F OCOC₆H₅ CH₃  102 bond Cl OCOC₆H₅ CH₃  103 bond Br OCOC₆H₅ CH₃  104 bond NO₂ OCOC₆H₅ CH₃  105 bond SCH₃ OCOC₆H₅ CH₃  106 bond SO₂CH₃ OCOC₆H₅ CH₃  107 bond SO₂CH₂CH₃ OCOC₆H₅ CH₃  108 bond CH₃ OCOC₆H₅ CH₃  109 bond CF₃ OCOC₆H₅ CH₃  110 bond OCHF₂ OCOC₆H₅ CH₃  111 CH₂ F OCOC₆H₅ CH₃  112 CH₂ Cl OCOC₆H₅ CH₃  113 CH₂ Br OCOC₆H₅ CH₃  114 CH₂ NO₂ OCOC₆H₅ CH₃  115 CH₂ SCH₃ OCOC₆H₅ CH₃  116 CH₂ SO₂CH₃ OCOC₆H₅ CH₃  117 CH₂ SO₂CH₂CH₃ OCOC₆H₅ CH₃  118 CH₂ CH₃ OCOC₆H₅ CH₃  119 CH₂ CF₃ OCOC₆H₅ CH₃  120 CH₂ OCHF₂ OCOC₆H₅ CH₃  121 O F OCOC₆H₅ CH₃  122 O Cl OCOC₆H₅ CH₃  123 O Br OCOC₆H₅ CH₃  124 O NO₂ OCOC₆H₅ CH₃  125 O SCH₃ OCOC₆H₅ CH₃  126 O SO₂CH₃ OCOC₆H₅ CH₃  127 O SO₂CH₂CH₃ OCOC₆H₅ CH₃  128 O CH₃ OCOC₆H₅ CH₃  129 O CF₃ OCOC₆H₅ CH₃  130 O OCHF₂ OCOC₆H₅ CH₃  131 S F OCOC₆H₅ CH₃  132 S Cl OCOC₆H₅ CH₃  133 S Br OCOC₆H₅ CH₃  134 S NO₂ OCOC₆H₅ CH₃  135 S SCH₃ OCOC₆H₅ CH₃  136 S SO₂CH₃ OCOC₆H₅ CH₃  137 S SO₂CH₂CH₃ OCOC₆H₅ CH₃  138 S CH₃ OCOC₆H₅ CH₃  139 S CF₃ OCOC₆H₅ CH₃  140 S OCHF₂ OCOC₆H₅ CH₃  141 SO₂ F OCOC₆H₅ CH₃  142 SO₂ Cl OCOC₆H₅ CH₃  143 SO₂ Br OCOC₆H₅ CH₃  144 SO₂ NO₂ OCOC₆H₅ CH₃  145 SO₂ SCH₃ OCOC₆H₅ CH₃  146 SO₂ SO₂CH₃ OCOC₆H₅ CH₃  147 SO₂ SO₂CH₂CH₃ OCOC₆H₅ CH₃  148 SO₂ CH₃ OCOC₆H₅ CH₃  149 SO₂ CF₃ OCOC₆H₅ CH₃  150 SO₂ OCHF₂ OCOC₆H₅ CH₃  151 bond F OCOC₆H₅ CH₂CH₃  152 bond Cl OCOC₆H₅ CH₂CH₃  153 bond Br OCOC₆H₅ CH₂CH₃  154 bond NO₂ OCOC₆H₅ CH₂CH₃  155 bond SCH₃ OCOC₆H₅ CH₂CH₃  156 bond SO₂CH₃ OCOC₆H₅ CH₂CH₃  157 bond SO₂CH₂CH₃ OCOC₆H₅ CH₂CH₃  158 bond CH₃ OCOC₆H₅ CH₂CH₃  159 bond CF₃ OCOC₆H₅ CH₂CH₃  160 bond OCHF₂ OCOC₆H₅ CH₂CH₃  161 CH₂ F OCOC₆H₅ CH₂CH₃  162 CH₂ Cl OCOC₆H₅ CH₂CH₃  163 CH₂ Br OCOC₆H₅ CH₂CH₃  164 CH₂ NO₂ OCOC₆H₅ CH₂CH₃  165 CH₂ SCH₃ OCOC₆H₅ CH₂CH₃  166 CH₂ SO₂CH₃ OCOC₆H₅ CH₂CH₃  167 CH₂ SO₂CH₂CH₃ OCOC₆H₅ CH₂CH₃  168 CH₂ CH₃ OCOC₆H₅ CH₂CH₃  169 CH₂ CF₃ OCOC₆H₅ CH₂CH₃  170 CH₂ OCHF₂ OCOC₆H₅ CH₂CH₃  171 O F OCOC₆H₅ CH₂CH₃  172 O Cl OCOC₆H₅ CH₂CH₃  173 O Br OCOC₆H₅ CH₂CH₃  174 O NO₂ OCOC₆H₅ CH₂CH₃  175 O SCH₃ OCOC₆H₅ CH₂CH₃  176 O SO₂CH₃ OCOC₆H₅ CH₂CH₃  177 O SO₂CH₂CH₃ OCOC₆H₅ CH₂CH₃  178 O CH₃ OCOC₆H₅ CH₂CH₃  179 O CF₃ OCOC₆H₅ CH₂CH₃  180 O OCHF₂ OCOC₆H₅ CH₂CH₃  181 S F OCOC₆H₅ CH₂CH₃  182 S Cl OCOC₆H₅ CH₂CH₃  183 S Br OCOC₆H₅ CH₂CH₃  184 S NO₂ OCOC₆H₅ CH₂CH₃  185 S SCH₃ OCOC₆H₅ CH₂CH₃  186 S SO₂CH₃ OCOC₆H₅ CH₂CH₃  187 S SO₂CH₂CH₃ OCOC₆H₅ CH₂CH₃  188 S CH₃ OCOC₆H₅ CH₂CH₃  189 S CF₃ OCOC₆H₅ CH₂CH₃  190 S OCHF₂ OCOC₆H₅ CH₂CH₃  191 SO₂ F OCOC₆H₅ CH₂CH₃  192 SO₂ Cl OCOC₆H₅ CH₂CH₃  193 SO₂ Br OCOC₆H₅ CH₂CH₃  194 SO₂ NO₂ OCOC₆H₅ CH₂CH₃  195 SO₂ SCH₃ OCOC₆H₅ CH₂CH₃  196 SO₂ SO₂CH₃ OCOC₆H₅ CH₂CH₃  197 SO₂ SO₂CH₂CH₃ OCOC₆H₅ CH₂CH₃  198 SO₂ CH₃ OCOC₆H₅ CH₂CH₃  199 SO₂ CF₃ OCOC₆H₅ CH₂CH₃  200 SO₂ OCHF₂ OCOC₆H₅ CH₂CH₃  201 bond F OCOC(CH₃)₃ CH₃  202 bond Cl OCOC(CH₃)₃ CH₃  203 bond Br OCOC(CH₃)₃ CH₃  204 bond NO₂ OCOC(CH₃)₃ CH₃  205 bond SCH₃ OCOC(CH₃)₃ CH₃  206 bond SO₂CH₃ OCOC(CH₃)₃ CH₃  207 bond SO₂CH₂CH₃ OCOC(CH₃)₃ CH₃  208 bond CH₃ OCOC(CH₃)₃ CH₃  209 bond CF₃ OCOC(CH₃)₃ CH₃  210 bond OCHF₂ OCOC(CH₃)₃ CH₃  211 CH₂ F OCOC(CH₃)₃ CH₃  212 CH₂ Cl OCOC(CH₃)₃ CH₃  213 CH₂ Br OCOC(CH₃)₃ CH₃  214 CH₂ NO₂ OCOC(CH₃)₃ CH₃  215 CH₂ SCH₃ OCOC(CH₃)₃ CH₃  216 CH₂ SO₂CH₃ OCOC(CH₃)₃ CH₃  217 CH₂ SO₂CH₂CH₃ OCOC(CH₃)₃ CH₃  218 CH₂ CH₃ OCOC(CH₃)₃ CH₃  219 CH₂ CF₃ OCOC(CH₃)₃ CH₃  220 CH₂ OCHF₂ OCOC(CH₃)₃ CH₃  221 O F OCOC(CH₃)₃ CH₃  222 O Cl OCOC(CH₃)₃ CH₃  223 O Br OCOC(CH₃)₃ CH₃  224 O NO₂ OCOC(CH₃)₃ CH₃  225 O SCH₃ OCOC(CH₃)₃ CH₃  226 O SO₂CH₃ OCOC(CH₃)₃ CH₃  227 O SO₂CH₂CH₃ OCOC(CH₃)₃ CH₃  228 O CH₃ OCOC(CH₃)₃ CH₃  229 O CF₃ OCOC(CH₃)₃ CH₃  230 O OCHF₂ OCOC(CH₃)₃ CH₃  231 S F OCOC(CH₃)₃ CH₃  232 S Cl OCOC(CH₃)₃ CH₃  233 S Br OCOC(CH₃)₃ CH₃  234 S NO₂ OCOC(CH₃)₃ CH₃  235 S SCH₃ OCOC(CH₃)₃ CH₃  236 S SO₂CH₃ OCOC(CH₃)₃ CH₃  237 S SO₂CH₂CH₃ OCOC(CH₃)₃ CH₃  238 S CH₃ OCOC(CH₃)₃ CH₃  239 S CF₃ OCOC(CH₃)₃ CH₃  240 S OCHF₂ OCOC(CH₃)₃ CH₃  241 SO₂ F OCOC(CH₃)₃ CH₃  242 SO₂ Cl OCOC(CH₃)₃ CH₃  243 SO₂ Br OCOC(CH₃)₃ CH₃  244 SO₂ NO₂ OCOC(CH₃)₃ CH₃  245 SO₂ SCH₃ OCOC(CH₃)₃ CH₃  246 SO₂ SO₂CH₃ OCOC(CH₃)₃ CH₃  247 SO₂ SO₂CH₂CH₃ OCOC(CH₃)₃ CH₃  248 SO₂ CH₃ OCOC(CH₃)₃ CH₃  249 SO₂ CF₃ OCOC(CH₃)₃ CH₃  250 SO₂ OCHF₂ OCOC(CH₃)₃ CH₃  251 bond F OCOC(CH₃)₃ CH₂CH₃  252 bond Cl OCOC(CH₃)₃ CH₂CH₃  253 bond Br OCOC(CH₃)₃ CH₂CH₃  254 bond NO₂ OCOC(CH₃)₃ CH₂CH₃  255 bond SCH₃ OCOC(CH₃)₃ CH₂CH₃  256 bond SO₂CH₃ OCOC(CH₃)₃ CH₂CH₃  257 bond SO₂CH₂CH₃ OCOC(CH₃)₃ CH₂CH₃  258 bond CH₃ OCOC(CH₃)₃ CH₂CH₃  259 bond CF₃ OCOC(CH₃)₃ CH₂CH₃  260 bond OCHF₂ OCOC(CH₃)₃ CH₂CH₃  261 CH₂ F OCOC(CH₃)₃ CH₂CH₃  262 CH₂ Cl OCOC(CH₃)₃ CH₂CH₃  263 CH₂ Br OCOC(CH₃)₃ CH₂CH₃  264 CH₂ NO₂ OCOC(CH₃)₃ CH₂CH₃  265 CH₂ SCH₃ OCOC(CH₃)₃ CH₂CH₃  266 CH₂ SO₂CH₃ OCOC(CH₃)₃ CH₂CH₃  267 CH₂ SO₂CH₂CH₃ OCOC(CH₃)₃ CH₂CH₃  268 CH₂ CH₃ OCOC(CH₃)₃ CH₂CH₃  269 CH₂ CF₃ OCOC(CH₃)₃ CH₂CH₃  270 CH₂ OCHF₂ OCOC(CH₃)₃ CH₂CH₃  271 O F OCOC(CH₃)₃ CH₂CH₃  272 O Cl OCOC(CH₃)₃ CH₂CH₃  273 O Br OCOC(CH₃)₃ CH₂CH₃  274 O NO₂ OCOC(CH₃)₃ CH₂CH₃  275 O SCH₃ OCOC(CH₃)₃ CH₂CH₃  276 O SO₂CH₃ OCOC(CH₃)₃ CH₂CH₃  277 O SO₂CH₂CH₃ OCOC(CH₃)₃ CH₂CH₃  278 O CH₃ OCOC(CH₃)₃ CH₂CH₃  279 O CF₃ OCOC(CH₃)₃ CH₂CH₃  280 O OCHF₂ OCOC(CH₃)₃ CH₂CH₃  281 S F OCOC(CH₃)₃ CH₂CH₃  282 S Cl OCOC(CH₃)₃ CH₂CH₃  283 S Br OCOC(CH₃)₃ CH₂CH₃  284 S NO₂ OCOC(CH₃)₃ CH₂CH₃  285 S SCH₃ OCOC(CH₃)₃ CH₂CH₃  286 S SO₂CH₃ OCOC(CH₃)₃ CH₂CH₃  287 S SO₂CH₂CH₃ OCOC(CH₃)₃ CH₂CH₃  288 S CH₃ OCOC(CH₃)₃ CH₂CH₃  289 S CF₃ OCOC(CH₃)₃ CH₂CH₃  290 S OCHF₂ OCOC(CH₃)₃ CH₂CH₃  291 SO₂ F OCOC(CH₃)₃ CH₂CH₃  292 SO₂ Cl OCOC(CH₃)₃ CH₂CH₃  293 SO₂ Br OCOC(CH₃)₃ CH₂CH₃  294 SO₂ NO₂ OCOC(CH₃)₃ CH₂CH₃  295 SO₂ SCH₃ OCOC(CH₃)₃ CH₂CH₃  296 SO₂ SO₂CH₃ OCOC(CH₃)₃ CH₂CH₃  297 SO₂ SO₂CH₂CH₃ OCOC(CH₃)₃ CH₂CH₃  298 SO₂ CH₃ OCOC(CH₃)₃ CH₂CH₃  299 SO₂ CF₃ OCOC(CH₃)₃ CH₂CH₃  300 SO₂ OCHF₂ OCOC(CH₃)₃ CH₂CH₃  301 bond F OCOSCH₃ CH₃  302 bond Cl OCOSCH₃ CH₃  303 bond Br OCOSCH₃ CH₃  304 bond NO₂ OCOSCH₃ CH₃  305 bond SCH₃ OCOSCH₃ CH₃  306 bond SO₂CH₃ OCOSCH₃ CH₃  307 bond SO₂CH₂CH₃ OCOSCH₃ CH₃  308 bond CH₃ OCOSCH₃ CH₃  309 bond CF₃ OCOSCH₃ CH₃  310 bond OCHF₂ OCOSCH₃ CH₃  311 CH₂ F OCOSCH₃ CH₃  312 CH₂ Cl OCOSCH₃ CH₃  313 CH₂ Br OCOSCH₃ CH₃  314 CH₂ NO₂ OCOSCH₃ CH₃  315 CH₂ SCH₃ OCOSCH₃ CH₃  316 CH₂ SO₂CH₃ OCOSCH₃ CH₃  317 CH₂ SO₂CH₂CH₃ OCOSCH₃ CH₃  318 CH₂ CH₃ OCOSCH₃ CH₃  319 CH₂ CF₃ OCOSCH₃ CH₃  320 CH₂ OCHF₂ OCOSCH₃ CH₃  321 O F OCOSCH₃ CH₃  322 O Cl OCOSCH₃ CH₃  323 O Br OCOSCH₃ CH₃  324 O NO₂ OCOSCH₃ CH₃  325 O SCH₃ OCOSCH₃ CH₃  326 O SO₂CH₃ OCOSCH₃ CH₃  327 O SO₂CH₂CH₃ OCOSCH₃ CH₃  328 O CH₃ OCOSCH₃ CH₃  329 O CF₃ OCOSCH₃ CH₃  330 O OCHF₂ OCOSCH₃ CH₃  331 S F OCOSCH₃ CH₃  332 S Cl OCOSCH₃ CH₃  333 S Br OCOSCH₃ CH₃  334 S NO₂ OCOSCH₃ CH₃  335 S SCH₃ OCOSCH₃ CH₃  336 S SO₂CH₃ OCOSCH₃ CH₃  337 S SO₂CH₂CH₃ OCOSCH₃ CH₃  338 S CH₃ OCOSCH₃ CH₃  339 S CF₃ OCOSCH₃ CH₃  340 S OCHF₂ OCOSCH₃ CH₃  341 SO₂ F OCOSCH₃ CH₃  342 SO₂ Cl OCOSCH₃ CH₃  343 SO₂ Br OCOSCH₃ CH₃  344 SO₂ NO₂ OCOSCH₃ CH₃  345 SO₂ SCH₃ OCOSCH₃ CH₃  346 SO₂ SO₂CH₃ OCOSCH₃ CH₃  347 SO₂ SO₂CH₂CH₃ OCOSCH₃ CH₃  348 SO₂ CH₃ OCOSCH₃ CH₃  349 SO₂ CF₃ OCOSCH₃ CH₃  350 SO₂ OCHF₂ OCOSCH₃ CH₃  351 bond F OCOSCH₃ CH₂CH₃  352 bond Cl OCOSCH₃ CH₂CH₃  353 bond Br OCOSCH₃ CH₂CH₃  354 bond NO₂ OCOSCH₃ CH₂CH₃  355 bond SCH₃ OCOSCH₃ CH₂CH₃  356 bond SO₂CH₃ OCOSCH₃ CH₂CH₃  357 bond SO₂CH₂CH₃ OCOSCH₃ CH₂CH₃  358 bond CH₃ OCOSCH₃ CH₂CH₃  359 bond CF₃ OCOSCH₃ CH₂CH₃  360 bond OCHF₂ OCOSCH₃ CH₂CH₃  361 CH₂ F OCOSCH₃ CH₂CH₃  362 CH₂ Cl OCOSCH₃ CH₂CH₃  363 CH₂ Br OCOSCH₃ CH₂CH₃  364 CH₂ NO₂ OCOSCH₃ CH₂CH₃  365 CH₂ SCH₃ OCOSCH₃ CH₂CH₃  366 CH₂ SO₂CH₃ OCOSCH₃ CH₂CH₃  367 CH₂ SO₂CH₂CH₃ OCOSCH₃ CH₂CH₃  368 CH₂ CH₃ OCOSCH₃ CH₂CH₃  369 CH₂ CF₃ OCOSCH₃ CH₂CH₃  370 CH₂ OCHF₂ OCOSCH₃ CH₂CH₃  371 O F OCOSCH₃ CH₂CH₃  372 O Cl OCOSCH₃ CH₂CH₃  373 O Br OCOSCH₃ CH₂CH₃  374 O NO₂ OCOSCH₃ CH₂CH₃  375 O SCH₃ OCOSCH₃ CH₂CH₃  376 O SO₂CH₃ OCOSCH₃ CH₂CH₃  377 O SO₂CH₂CH₃ OCOSCH₃ CH₂CH₃  378 O CH₃ OCOSCH₃ CH₂CH₃  379 O CF₃ OCOSCH₃ CH₂CH₃  380 O OCHF₂ OCOSCH₃ CH₂CH₃  381 S F OCOSCH₃ CH₂CH₃  382 S Cl OCOSCH₃ CH₂CH₃  383 S Br OCOSCH₃ CH₂CH₃  384 S NO₂ OCOSCH₃ CH₂CH₃  385 S SCH₃ OCOSCH₃ CH₂CH₃  386 S SO₂CH₃ OCOSCH₃ CH₂CH₃  387 S SO₂CH₂CH₃ OCOSCH₃ CH₂CH₃  388 S CH₃ OCOSCH₃ CH₂CH₃  389 S CF₃ OCOSCH₃ CH₂CH₃  390 S OCHF₂ OCOSCH₃ CH₂CH₃  391 SO₂ F OCOSCH₃ CH₂CH₃  392 SO₂ Cl OCOSCH₃ CH₂CH₃  393 SO₂ Br OCOSCH₃ CH₂CH₃  394 SO₂ NO₂ OCOSCH₃ CH₂CH₃  395 SO₂ SCH₃ OCOSCH₃ CH₂CH₃  396 SO₂ SO₂CH₃ OCOSCH₃ CH₂CH₃  397 SO₂ SO₂CH₂CH₃ OCOSCH₃ CH₂CH₃  398 SO₂ CH₃ OCOSCH₃ CH₂CH₃  399 SO₂ CF₃ OCOSCH₃ CH₂CH₃  400 SO₂ OCHF₂ OCOSCH₃ CH₂CH₃  401 bond F OCH₃ CH₃  402 bond Cl OCH₃ CH₃  403 bond Br OCH₃ CH₃  404 bond NO₂ OCH₃ CH₃  405 bond SCH₃ OCH₃ CH₃  406 bond SO₂CH₃ OCH₃ CH₃  407 bond SO₂CH₂CH₃ OCH₃ CH₃  408 bond CH₃ OCH₃ CH₃  409 bond CF₃ OCH₃ CH₃  410 bond OCHF₂ OCH₃ CH₃  411 CH₂ F OCH₃ CH₃  412 CH₂ Cl OCH₃ CH₃  413 CH₂ Br OCH₃ CH₃  414 CH₂ NO₂ OCH₃ CH₃  415 CH₂ SCH₃ OCH₃ CH₃  416 CH₂ SO₂CH₃ OCH₃ CH₃  417 CH₂ SO₂CH₂CH₃ OCH₃ CH₃  418 CH₂ CH₃ OCH₃ CH₃  419 CH₂ CF₃ OCH₃ CH₃  420 CH₂ OCHF₂ OCH₃ CH₃  421 O F OCH₃ CH₃  422 O Cl OCH₃ CH₃  423 O Br OCH₃ CH₃  424 O NO₂ OCH₃ CH₃  425 O SCH₃ OCH₃ CH₃  426 O SO₂CH₃ OCH₃ CH₃  427 O SO₂CH₂CH₃ OCH₃ CH₃  428 O CH₃ OCH₃ CH₃  429 O CF₃ OCH₃ CH₃  430 O OCHF₂ OCH₃ CH₃  431 S F OCH₃ CH₃  432 S Cl OCH₃ CH₃  433 S Br OCH₃ CH₃  434 S NO₂ OCH₃ CH₃  435 S SCH₃ OCH₃ CH₃  436 S SO₂CH₃ OCH₃ CH₃  437 S SO₂CH₂CH₃ OCH₃ CH₃  438 S CH₃ OCH₃ CH₃  439 S CF₃ OCH₃ CH₃  440 S OCHF₂ OCH₃ CH₃  441 SO₂ F OCH₃ CH₃  442 SO₂ Cl OCH₃ CH₃  443 SO₂ Br OCH₃ CH₃  444 SO₂ NO₂ OCH₃ CH₃  445 SO₂ SCH₃ OCH₃ CH₃  446 SO₂ SO₂CH₃ OCH₃ CH₃  447 SO₂ SO₂CH₂CH₃ OCH₃ CH₃  448 SO₂ CH₃ OCH₃ CH₃  449 SO₂ CF₃ OCH₃ CH₃  450 SO₂ OCHF₂ OCH₃ CH₃  451 bond F OCH₃ CH₂CH₃  452 bond Cl OCH₃ CH₂CH₃  453 bond Br OCH₃ CH₂CH₃  454 bond NO₂ OCH₃ CH₂CH₃  455 bond SCH₃ OCH₃ CH₂CH₃  456 bond SO₂CH₃ OCH₃ CH₂CH₃  457 bond SO₂CH₂CH₃ OCH₃ CH₂CH₃  458 bond CH₃ OCH₃ CH₂CH₃  459 bond CF₃ OCH₃ CH₂CH₃  460 bond OCHF₂ OCH₃ CH₂CH₃  461 CH₂ F OCH₃ CH₂CH₃  462 CH₂ Cl OCH₃ CH₂CH₃  463 CH₂ Br OCH₃ CH₂CH₃  464 CH₂ NO₂ OCH₃ CH₂CH₃  465 CH₂ SCH₃ OCH₃ CH₂CH₃  466 CH₂ SO₂CH₃ OCH₃ CH₂CH₃  467 CH₂ SO₂CH₂CH₃ OCH₃ CH₂CH₃  468 CH₂ CH₃ OCH₃ CH₂CH₃  469 CH₂ CF₃ OCH₃ CH₂CH₃  470 CH₂ OCHF₂ OCH₃ CH₂CH₃  471 O F OCH₃ CH₂CH₃  472 O Cl OCH₃ CH₂CH₃  473 O Br OCH₃ CH₂CH₃  474 O NO₂ OCH₃ CH₂CH₃  475 O SCH₃ OCH₃ CH₂CH₃  476 O SO₂CH₃ OCH₃ CH₂CH₃  477 O SO₂CH₂CH₃ OCH₃ CH₂CH₃  478 O CH₃ OCH₃ CH₂CH₃  479 O CF₃ OCH₃ CH₂CH₃  480 O OCHF₂ OCH₃ CH₂CH₃  481 S F OCH₃ CH₂CH₃  482 S Cl OCH₃ CH₂CH₃  483 S Br OCH₃ CH₂CH₃  484 S NO₂ OCH₃ CH₂CH₃  485 S SCH₃ OCH₃ CH₂CH₃  486 S SO₂CH₃ OCH₃ CH₂CH₃  487 S SO₂CH₂CH₃ OCH₃ CH₂CH₃  488 S CH₃ OCH₃ CH₂CH₃  489 S CF₃ OCH₃ CH₂CH₃  490 S OCHF₂ OCH₃ CH₂CH₃  491 SO₂ F OCH₃ CH₂CH₃  492 SO₂ Cl OCH₃ CH₂CH₃  493 SO₂ Br OCH₃ CH₂CH₃  494 SO₂ NO₂ OCH₃ CH₂CH₃  495 SO₂ SCH₃ OCH₃ CH₂CH₃  496 SO₂ SO₂CH₃ OCH₃ CH₂CH₃  497 SO₂ SO₂CH₂CH₃ OCH₃ CH₂CH₃  498 SO₂ CH₃ OCH₃ CH₂CH₃  499 SO₂ CF₃ OCH₃ CH₂CH₃  500 SO₂ OCHF₂ OCH₃ CH₂CH₃  501 bond F OCH(CH₃)₂ CH₃  502 bond Cl OCH(CH₃)₂ CH₃  503 bond Br OCH(CH₃)₂ CH₃  504 bond NO₂ OCH(CH₃)₂ CH₃  505 bond SCH₃ OCH(CH₃)₂ CH₃  506 bond SO₂CH₃ OCH(CH₃)₂ CH₃  507 bond SO₂CH₂CH₃ OCH(CH₃)₂ CH₃  508 bond CH₃ OCH(CH₃)₂ CH₃  509 bond CF₃ OCH(CH₃)₂ CH₃  510 bond OCHF₂ OCH(CH₃)₂ CH₃  511 CH₂ F OCH(CH₃)₂ CH₃  512 CH₂ Cl OCH(CH₃)₂ CH₃  513 CH₂ Br OCH(CH₃)₂ CH₃  514 CH₂ NO₂ OCH(CH₃)₂ CH₃  515 CH₂ SCH₃ OCH(CH₃)₂ CH₃  516 CH₂ SO₂CH₃ OCH(CH₃)₂ CH₃  517 CH₂ SO₂CH₂CH₃ OCH(CH₃)₂ CH₃  518 CH₂ CH₃ OCH(CH₃)₂ CH₃  519 CH₂ CF₃ OCH(CH₃)₂ CH₃  520 CH₂ OCHF₂ OCH(CH₃)₂ CH₃  521 O F OCH(CH₃)₂ CH₃  522 O Cl OCH(CH₃)₂ CH₃  523 O Br OCH(CH₃)₂ CH₃  524 O NO₂ OCH(CH₃)₂ CH₃  525 O SCH₃ OCH(CH₃)₂ CH₃  526 O SO₂CH₃ OCH(CH₃)₂ CH₃  527 O SO₂CH₂CH₃ OCH(CH₃)₂ CH₃  528 O CH₃ OCH(CH₃)₂ CH₃  529 O CF₃ OCH(CH₃)₂ CH₃  530 O OCHF₂ OCH(CH₃)₂ CH₃  531 S F OCH(CH₃)₂ CH₃  532 S Cl OCH(CH₃)₂ CH₃  533 S Br OCH(CH₃)₂ CH₃  534 S NO₂ OCH(CH₃)₂ CH₃  535 S SCH₃ OCH(CH₃)₂ CH₃  536 S SO₂CH₃ OCH(CH₃)₂ CH₃  537 S SO₂CH₂CH₃ OCH(CH₃)₂ CH₃  538 S CH₃ OCH(CH₃)₂ CH₃  539 S CF₃ OCH(CH₃)₂ CH₃  540 S OCHF₂ OCH(CH₃)₂ CH₃  541 SO₂ F OCH(CH₃)₂ CH₃  542 SO₂ Cl OCH(CH₃)₂ CH₃  543 SO₂ Br OCH(CH₃)₂ CH₃  544 SO₂ NO₂ OCH(CH₃)₂ CH₃  545 SO₂ SCH₃ OCH(CH₃)₂ CH₃  546 SO₂ SO₂CH₃ OCH(CH₃)₂ CH₃  547 SO₂ SO₂CH₂CH₃ OCH(CH₃)₂ CH₃  548 SO₂ CH₃ OCH(CH₃)₂ CH₃  549 SO₂ CF₃ OCH(CH₃)₂ CH₃  550 SO₂ OCHF₂ OCH(CH₃)₂ CH₃  551 bond F OCH(CH₃)₂ CH₂CH₃  552 bond Cl OCH(CH₃)₂ CH₂CH₃  553 bond Br OCH(CH₃)₂ CH₂CH₃  554 bond NO₂ OCH(CH₃)₂ CH₂CH₃  555 bond SCH₃ OCH(CH₃)₂ CH₂CH₃  556 bond SO₂CH₃ OCH(CH₃)₂ CH₂CH₃  557 bond SO₂CH₂CH₃ OCH(CH₃)₂ CH₂CH₃  558 bond CH₃ OCH(CH₃)₂ CH₂CH₃  559 bond CF₃ OCH(CH₃)₂ CH₂CH₃  560 bond OCHF₂ OCH(CH₃)₂ CH₂CH₃  561 CH₂ F OCH(CH₃)₂ CH₂CH₃  562 CH₂ Cl OCH(CH₃)₂ CH₂CH₃  563 CH₂ Br OCH(CH₃)₂ CH₂CH₃  564 CH₂ NO₂ OCH(CH₃)₂ CH₂CH₃  565 CH₂ SCH₃ OCH(CH₃)₂ CH₂CH₃  566 CH₂ SO₂CH₃ OCH(CH₃)₂ CH₂CH₃  567 CH₂ SO₂CH₂CH₃ OCH(CH₃)₂ CH₂CH₃  568 CH₂ CH₃ OCH(CH₃)₂ CH₂CH₃  569 CH₂ CF₃ OCH(CH₃)₂ CH₂CH₃  570 CH₂ OCHF₂ OCH(CH₃)₂ CH₂CH₃  571 O F OCH(CH₃)₂ CH₂CH₃  572 O Cl OCH(CH₃)₂ CH₂CH₃  573 O Br OCH(CH₃)₂ CH₂CH₃  574 O NO₂ OCH(CH₃)₂ CH₂CH₃  575 O SCH₃ OCH(CH₃)₂ CH₂CH₃  576 O SO₂CH₃ OCH(CH₃)₂ CH₂CH₃  577 O SO₂CH₂CH₃ OCH(CH₃)₂ CH₂CH₃  578 O CH₃ OCH(CH₃)₂ CH₂CH₃  579 O CF₃ OCH(CH₃)₂ CH₂CH₃  580 O OCHF₂ OCH(CH₃)₂ CH₂CH₃  581 S F OCH(CH₃)₂ CH₂CH₃  582 S Cl OCH(CH₃)₂ CH₂CH₃  583 S Br OCH(CH₃)₂ CH₂CH₃  584 S NO₂ OCH(CH₃)₂ CH₂CH₃  585 S SCH₃ OCH(CH₃)₂ CH₂CH₃  586 S SO₂CH₃ OCH(CH₃)₂ CH₂CH₃  587 S SO₂CH₂CH₃ OCH(CH₃)₂ CH₂CH₃  588 S CH₃ OCH(CH₃)₂ CH₂CH₃  589 S CF₃ OCH(CH₃)₂ CH₂CH₃  590 S OCHF₂ OCH(CH₃)₂ CH₂CH₃  591 SO₂ F OCH(CH₃)₂ CH₂CH₃  592 SO₂ Cl OCH(CH₃)₂ CH₂CH₃  593 SO₂ Br OCH(CH₃)₂ CH₂CH₃  594 SO₂ NO₂ OCH(CH₃)₂ CH₂CH₃  595 SO₂ SCH₃ OCH(CH₃)₂ CH₂CH₃  596 SO₂ SO₂CH₃ OCH(CH₃)₂ CH₂CH₃  597 SO₂ SO₂CH₂CH₃ OCH(CH₃)₂ CH₂CH₃  598 SO₂ CH₃ OCH(CH₃)₂ CH₂CH₃  599 SO₂ CF₃ OCH(CH₃)₂ CH₂CH₃  600 SO₂ OCHF₂ OCH(CH₃)₂ CH₂CH₃  601 bond F OCH₂C₆H₅ CH₃  602 bond Cl OCH₂C₆H₅ CH₃  603 bond Br OCH₂C₆H₅ CH₃  604 bond NO₂ OCH₂C₆H₅ CH₃  605 bond SCH₃ OCH₂C₆H₅ CH₃  606 bond SO₂CH₃ OCH₂C₆H₅ CH₃  607 bond SO₂CH₂CH₃ OCH₂C₆H₅ CH₃  608 bond CH₃ OCH₂C₆H₅ CH₃  609 bond CF₃ OCH₂C₆H₅ CH₃  610 bond OCHF₂ OCH₂C₆H₅ CH₃  611 CH₂ F OCH₂C₆H₅ CH₃  612 CH₂ Cl OCH₂C₆H₅ CH₃  613 CH₂ Br OCH₂C₆H₅ CH₃  614 CH₂ NO₂ OCH₂C₆H₅ CH₃  615 CH₂ SCH₃ OCH₂C₆H₅ CH₃  616 CH₂ SO₂CH₃ OCH₂C₆H₅ CH₃  617 CH₂ SO₂CH₂CH₃ OCH₂C₆H₅ CH₃  618 CH₂ CH₃ OCH₂C₆H₅ CH₃  619 CH₂ CF₃ OCH₂C₆H₅ CH₃  620 CH₂ OCHF₂ OCH₂C₆H₅ CH₃  621 O F OCH₂C₆H₅ CH₃  622 O Cl OCH₂C₆H₅ CH₃  623 O Br OCH₂C₆H₅ CH₃  624 O NO₂ OCH₂C₆H₅ CH₃  625 O SCH₃ OCH₂C₆H₅ CH₃  626 O SO₂CH₃ OCH₂C₆H₅ CH₃  627 O SO₂CH₂CH₃ OCH₂C₆H₅ CH₃  628 O CH₃ OCH₂C₆H₅ CH₃  629 O CF₃ OCH₂C₆H₅ CH₃  630 O OCHF₂ OCH₂C₆H₅ CH₃  631 S F OCH₂C₆H₅ CH₃  632 S Cl OCH₂C₆H₅ CH₃  633 S Br OCH₂C₆H₅ CH₃  634 S NO₂ OCH₂C₆H₅ CH₃  635 S SCH₃ OCH₂C₆H₅ CH₃  636 S SO₂CH₃ OCH₂C₆H₅ CH₃  637 S SO₂CH₂CH₃ OCH₂C₆H₅ CH₃  638 S CH₃ OCH₂C₆H₅ CH₃  639 S CF₃ OCH₂C₆H₅ CH₃  640 S OCHF₂ OCH₂C₆H₅ CH₃  641 SO₂ F OCH₂C₆H₅ CH₃  642 SO₂ Cl OCH₂C₆H₅ CH₃  643 SO₂ Br OCH₂C₆H₅ CH₃  644 SO₂ NO₂ OCH₂C₆H₅ CH₃  645 SO₂ SCH₃ OCH₂C₆H₅ CH₃  646 SO₂ SO₂CH₃ OCH₂C₆H₅ CH₃  647 SO₂ SO₂CH₂CH₃ OCH₂C₆H₅ CH₃  648 SO₂ CH₃ OCH₂C₆H₅ CH₃  649 SO₂ CF₃ OCH₂C₆H₅ CH₃  650 SO₂ OCHF₂ OCH₂C₆H₅ CH₃  651 bond F OCH₂C₆H₅ CH₂CH₃  652 bond Cl OCH₂C₆H₅ CH₂CH₃  653 bond Br OCH₂C₆H₅ CH₂CH₃  654 bond NO₂ OCH₂C₆H₅ CH₂CH₃  655 bond SCH₃ OCH₂C₆H₅ CH₂CH₃  656 bond SO₂CH₃ OCH₂C₆H₅ CH₂CH₃  657 bond SO₂CH₂CH₃ OCH₂C₆H₅ CH₂CH₃  658 bond CH₃ OCH₂C₆H₅ CH₂CH₃  659 bond CF₃ OCH₂C₆H₅ CH₂CH₃  660 bond OCHF₂ OCH₂C₆H₅ CH₂CH₃  661 CH₂ F OCH₂C₆H₅ CH₂CH₃  662 CH₂ Cl OCH₂C₆H₅ CH₂CH₃  663 CH₂ Br OCH₂C₆H₅ CH₂CH₃  664 CH₂ NO₂ OCH₂C₆H₅ CH₂CH₃  665 CH₂ SCH₃ OCH₂C₆H₅ CH₂CH₃  666 CH₂ SO₂CH₃ OCH₂C₆H₅ CH₂CH₃  667 CH₂ SO₂CH₂CH₃ OCH₂C₆H₅ CH₂CH₃  668 CH₂ CH₃ OCH₂C₆H₅ CH₂CH₃  669 CH₂ CF₃ OCH₂C₆H₅ CH₂CH₃  670 CH₂ OCHF₂ OCH₂C₆H₅ CH₂CH₃  671 O F OCH₂C₆H₅ CH₂CH₃  672 O Cl OCH₂C₆H₅ CH₂CH₃  673 O Br OCH₂C₆H₅ CH₂CH₃  674 O NO₂ OCH₂C₆H₅ CH₂CH₃  675 O SCH₃ OCH₂C₆H₅ CH₂CH₃  676 O SO₂CH₃ OCH₂C₆H₅ CH₂CH₃  677 O SO₂CH₂CH₃ OCH₂C₆H₅ CH₂CH₃  678 O CH₃ OCH₂C₆H₅ CH₂CH₃  679 O CF₃ OCH₂C₆H₅ CH₂CH₃  680 O OCHF₂ OCH₂C₆H₅ CH₂CH₃  681 S F OCH₂C₆H₅ CH₂CH₃  682 S Cl OCH₂C₆H₅ CH₂CH₃  683 S Br OCH₂C₆H₅ CH₂CH₃  684 S NO₂ OCH₂C₆H₅ CH₂CH₃  685 S SCH₃ OCH₂C₆H₅ CH₂CH₃  686 S SO₂CH₃ OCH₂C₆H₅ CH₂CH₃  687 S SO₂CH₂CH₃ OCH₂C₆H₅ CH₂CH₃  688 S CH₃ OCH₂C₆H₅ CH₂CH₃  689 S CF₃ OCH₂C₆H₅ CH₂CH₃  690 S OCHF₂ OCH₂C₆H₅ CH₂CH₃  691 SO₂ F OCH₂C₆H₅ CH₂CH₃  692 SO₂ Cl OCH₂C₆H₅ CH₂CH₃  693 SO₂ Br OCH₂C₆H₅ CH₂CH₃  694 SO₂ NO₂ OCH₂C₆H₅ CH₂CH₃  695 SO₂ SCH₃ OCH₂C₆H₅ CH₂CH₃  696 SO₂ SO₂CH₃ OCH₂C₆H₅ CH₂CH₃  697 SO₂ SO₂CH₂CH₃ OCH₂C₆H₅ CH₂CH₃  698 SO₂ CH₃ OCH₂C₆H₅ CH₂CH₃  699 SO₂ CF₃ OCH₂C₆H₅ CH₂CH₃  700 SO₂ OCHF₂ OCH₂C₆H₅ CH₂CH₃  701 bond F OSO₂(4-CH₃—C₆H₄) CH₃  702 bond Cl OSO₂(4-CH₃—C₆H₄) CH₃  703 bond Br OSO₂(4-CH₃—C₆H₄) CH₃  704 bond NO₂ OSO₂(4-CH₃—C₆H₄) CH₃  705 bond SCH₃ OSO₂(4-CH₃—C₆H₄) CH₃  706 bond SO₂CH₃ OSO₂(4-CH₃—C₆H₄) CH₃  707 bond SO₂CH₂CH₃ OSO₂(4-CH₃—C₆H₄) CH₃  708 bond CH₃ OSO₂(4-CH₃—C₆H₄) CH₃  709 bond CF₃ OSO₂(4-CH₃—C₆H₄) CH₃  710 bond OCHF₂ OSO₂(4-CH₃—C₆H₄) CH₃  711 CH₂ F OSO₂(4-CH₃—C₆H₄) CH₃  712 CH₂ Cl OSO₂(4-CH₃—C₆H₄) CH₃  713 CH₂ Br OSO₂(4-CH₃—C₆H₄) CH₃  714 CH₂ NO₂ OSO₂(4-CH₃—C₆H₄) CH₃  715 CH₂ SCH₃ OSO₂(4-CH₃—C₆H₄) CH₃  716 CH₂ SO₂CH₃ OSO₂(4-CH₃—C₆H₄) CH₃  717 CH₂ SO₂CH₂CH₃ OSO₂(4-CH₃—C₆H₄) CH₃  718 CH₂ CH₃ OSO₂(4-CH₃—C₆H₄) CH₃  719 CH₂ CF₃ OSO₂(4-CH₃—C₆H₄) CH₃  720 CH₂ OCHF₂ OSO₂(4-CH₃—C₆H₄) CH₃  721 O F OSO₂(4-CH₃—C₆H₄) CH₃  722 O Cl OSO₂(4-CH₃—C₆H₄) CH₃  723 O Br OSO₂(4-CH₃—C₆H₄) CH₃  724 O NO₂ OSO₂(4-CH₃—C₆H₄) CH₃  725 O SCH₃ OSO₂(4-CH₃—C₆H₄) CH₃  726 O SO₂CH₃ OSO₂(4-CH₃—C₆H₄) CH₃  727 O SO₂CH₂CH₃ OSO₂(4-CH₃—C₆H₄) CH₃  728 O CH₃ OSO₂(4-CH₃—C₆H₄) CH₃  729 O CF₃ OSO₂(4-CH₃—C₆H₄) CH₃  730 O OCHF₂ OSO₂(4-CH₃—C₆H₄) CH₃  731 S F OSO₂(4-CH₃—C₆H₄) CH₃  732 S Cl OSO₂(4-CH₃—C₆H₄) CH₃  733 S Br OSO₂(4-CH₃—C₆H₄) CH₃  734 S NO₂ OSO₂(4-CH₃—C₆H₄) CH₃  735 S SCH₃ OSO₂(4-CH₃—C₆H₄) CH₃  736 S SO₂CH₃ OSO₂(4-CH₃—C₆H₄) CH₃  737 S SO₂CH₂CH₃ OSO₂(4-CH₃—C₆H₄) CH₃  738 S CH₃ OSO₂(4-CH₃—C₆H₄) CH₃  739 S CF₃ OSO₂(4-CH₃—C₆H₄) CH₃  740 S OCHF₂ OSO₂(4-CH₃—C₆H₄) CH₃  741 SO₂ F OSO₂(4-CH₃—C₆H₄) CH₃  742 SO₂ Cl OSO₂(4-CH₃—C₆H₄) CH₃  743 SO₂ Br OSO₂(4-CH₃—C₆H₄) CH₃  744 SO₂ NO₂ OSO₂(4-CH₃—C₆H₄) CH₃  745 SO₂ SCH₃ OSO₂(4-CH₃—C₆H₄) CH₃  746 SO₂ SO₂CH₃ OSO₂(4-CH₃—C₆H₄) CH₃  747 SO₂ SO₂CH₂CH₃ OSO₂(4-CH₃—C₆H₄) CH₃  748 SO₂ CH₃ OSO₂(4-CH₃—C₆H₄) CH₃  749 SO₂ CF₃ OSO₂(4-CH₃—C₆H₄) CH₃  750 SO₂ OCHF₂ OSO₂(4-CH₃—C₆H₄) CH₃  751 bond F OSO₂(4-CH₃—C₆H₄) CH₂CH₃  752 bond Cl OSO₂(4-CH₃—C₆H₄) CH₂CH₃  753 bond Br OSO₂(4-CH₃—C₆H₄) CH₂CH₃  754 bond NO₂ OSO₂(4-CH₃—C₆H₄) CH₂CH₃  755 bond SCH₃ OSO₂(4-CH₃—C₆H₄) CH₂CH₃  756 bond SO₂CH₃ OSO₂(4-CH₃—C₆H₄) CH₂CH₃  757 bond SO₂CH₂CH₃ OSO₂(4-CH₃—C₆H₄) CH₂CH₃  758 bond CH₃ OSO₂(4-CH₃—C₆H₄) CH₂CH₃  759 bond CF₃ OSO₂(4-CH₃—C₆H₄) CH₂CH₃  760 bond OCHF₂ OSO₂(4-CH₃—C₆H₄) CH₂CH₃  761 CH₂ F OSO₂(4-CH₃—C₆H₄) CH₂CH₃  762 CH₂ Cl OSO₂(4-CH₃—C₆H₄) CH₂CH₃  763 CH₂ Br OSO₂(4-CH₃—C₆H₄) CH₂CH₃  764 CH₂ NO₂ OSO₂(4-CH₃—C₆H₄) CH₂CH₃  765 CH₂ SCH₃ OSO₂(4-CH₃—C₆H₄) CH₂CH₃  766 CH₂ SO₂CH₃ OSO₂(4-CH₃—C₆H₄) CH₂CH₃  767 CH₂ SO₂CH₂CH₃ OSO₂(4-CH₃—C₆H₄) CH₂CH₃  768 CH₂ CH₃ OSO₂(4-CH₃—C₆H₄) CH₂CH₃  769 CH₂ CF₃ OSO₂(4-CH₃—C₆H₄) CH₂CH₃  770 CH₂ OCHF₂ OSO₂(4-CH₃—C₆H₄) CH₂CH₃  771 O F OSO₂(4-CH₃—C₆H₄) CH₂CH₃  772 O Cl OSO₂(4-CH₃—C₆H₄) CH₂CH₃  773 O Br OSO₂(4-CH₃—C₆H₄) CH₂CH₃  774 O NO₂ OSO₂(4-CH₃—C₆H₄) CH₂CH₃  775 O SCH₃ OSO₂(4-CH₃—C₆H₄) CH₂CH₃  776 O SO₂CH₃ OSO₂(4-CH₃—C₆H₄) CH₂CH₃  777 O SO₂CH₂CH₃ OSO₂(4-CH₃—C₆H₄) CH₂CH₃  778 O CH₃ OSO₂(4-CH₃—C₆H₄) CH₂CH₃  779 O CF₃ OSO₂(4-CH₃—C₆H₄) CH₂CH₃  780 O OCHF₂ OSO₂(4-CH₃—C₆H₄) CH₂CH₃  781 S F OSO₂(4-CH₃—C₆H₄) CH₂CH₃  782 S Cl OSO₂(4-CH₃—C₆H₄) CH₂CH₃  783 S Br OSO₂(4-CH₃—C₆H₄) CH₂CH₃  784 S NO₂ OSO₂(4-CH₃—C₆H₄) CH₂CH₃  785 S SCH₃ OSO₂(4-CH₃—C₆H₄) CH₂CH₃  786 S SO₂CH₃ OSO₂(4-CH₃—C₆H₄) CH₂CH₃  787 S SO₂CH₂CH₃ OSO₂(4-CH₃—C₆H₄) CH₂CH₃  788 S CH₃ OSO₂(4-CH₃—C₆H₄) CH₂CH₃  789 S CF₃ OSO₂(4-CH₃—C₆H₄) CH₂CH₃  790 S OCHF₂ OSO₂(4-CH₃—C₆H₄) CH₂CH₃  791 SO₂ F OSO₂(4-CH₃—C₆H₄) CH₂CH₃  792 SO₂ Cl OSO₂(4-CH₃—C₆H₄) CH₂CH₃  793 SO₂ Br OSO₂(4-CH₃—C₆H₄) CH₂CH₃  794 SO₂ NO₂ OSO₂(4-CH₃—C₆H₄) CH₂CH₃  795 SO₂ SCH₃ OSO₂(4-CH₃—C₆H₄) CH₂CH₃  796 SO₂ SO₂CH₃ OSO₂(4-CH₃—C₆H₄) CH₂CH₃  797 SO₂ SO₂CH₂CH₃ OSO₂(4-CH₃—C₆H₄) CH₂CH₃  798 SO₂ CH₃ OSO₂(4-CH₃—C₆H₄) CH₂CH₃  799 SO₂ CF₃ OSO₂(4-CH₃—C₆H₄) CH₂CH₃  800 SO₂ OCHF₂ OSO₂(4-CH₃—C₆H₄) CH₂CH₃  801 bond F SCH₃ CH₃  802 bond Cl SCH₃ CH₃  803 bond Br SCH₃ CH₃  804 bond NO₂ SCH₃ CH₃  805 bond SCH₃ SCH₃ CH₃  806 bond SO₂CH₃ SCH₃ CH₃  807 bond SO₂CH₂CH₃ SCH₃ CH₃  808 bond CH₃ SCH₃ CH₃  809 bond CF₃ SCH₃ CH₃  810 bond OCHF₂ SCH₃ CH₃  811 CH₂ F SCH₃ CH₃  812 CH₂ Cl SCH₃ CH₃  813 CH₂ Br SCH₃ CH₃  814 CH₂ NO₂ SCH₃ CH₃  815 CH₂ SCH₃ SCH₃ CH₃  816 CH₂ SO₂CH₃ SCH₃ CH₃  817 CH₂ SO₂CH₂CH₃ SCH₃ CH₃  818 CH₂ CH₃ SCH₃ CH₃  819 CH₂ CF₃ SCH₃ CH₃  820 CH₂ OCHF₂ SCH₃ CH₃  821 O F SCH₃ CH₃  822 O Cl SCH₃ CH₃  823 O Br SCH₃ CH₃  824 O NO₂ SCH₃ CH₃  825 O SCH₃ SCH₃ CH₃  826 O SO₂CH₃ SCH₃ CH₃  827 O SO₂CH₂CH₃ SCH₃ CH₃  828 O CH₃ SCH₃ CH₃  829 O CF₃ SCH₃ CH₃  830 O OCHF₂ SCH₃ CH₃  831 S F SCH₃ CH₃  832 S Cl SCH₃ CH₃  833 S Br SCH₃ CH₃  834 S NO₂ SCH₃ CH₃  835 S SCH₃ SCH₃ CH₃  836 S SO₂CH₃ SCH₃ CH₃  837 S SO₂CH₂CH₃ SCH₃ CH₃  838 S CH₃ SCH₃ CH₃  839 S CF₃ SCH₃ CH₃  840 S OCHF₂ SCH₃ CH₃  841 SO₂ F SCH₃ CH₃  842 SO₂ Cl SCH₃ CH₃  843 SO₂ Br SCH₃ CH₃  844 SO₂ NO₂ SCH₃ CH₃  845 SO₂ SCH₃ SCH₃ CH₃  846 SO₂ SO₂CH₃ SCH₃ CH₃  847 SO₂ SO₂CH₂CH₃ SCH₃ CH₃  848 SO₂ CH₃ SCH₃ CH₃  849 SO₂ CF₃ SCH₃ CH₃  850 SO₂ OCHF₂ SCH₃ CH₃  851 bond F SCH₃ CH₂CH₃  852 bond Cl SCH₃ CH₂CH₃  853 bond Br SCH₃ CH₂CH₃  854 bond NO₂ SCH₃ CH₂CH₃  855 bond SCH₃ SCH₃ CH₂CH₃  856 bond SO₂CH₃ SCH₃ CH₂CH₃  857 bond SO₂CH₂CH₃ SCH₃ CH₂CH₃  858 bond CH₃ SCH₃ CH₂CH₃  859 bond CF₃ SCH₃ CH₂CH₃  860 bond OCHF₂ SCH₃ CH₂CH₃  861 CH₂ F SCH₃ CH₂CH₃  862 CH₂ Cl SCH₃ CH₂CH₃  863 CH₂ Br SCH₃ CH₂CH₃  864 CH₂ NO₂ SCH₃ CH₂CH₃  865 CH₂ SCH₃ SCH₃ CH₂CH₃  866 CH₂ SO₂CH₃ SCH₃ CH₂CH₃  867 CH₂ SO₂CH₂CH₃ SCH₃ CH₂CH₃  868 CH₂ CH₃ SCH₃ CH₂CH₃  869 CH₂ CF₃ SCH₃ CH₂CH₃  870 CH₂ OCHF₂ SCH₃ CH₂CH₃  871 O F SCH₃ CH₂CH₃  872 O Cl SCH₃ CH₂CH₃  873 O Br SCH₃ CH₂CH₃  874 O NO₂ SCH₃ CH₂CH₃  875 O SCH₃ SCH₃ CH₂CH₃  876 O SO₂CH₃ SCH₃ CH₂CH₃  877 O SO₂CH₂CH₃ SCH₃ CH₂CH₃  878 O CH₃ SCH₃ CH₂CH₃  879 O CF₃ SCH₃ CH₂CH₃  880 O OCHF₂ SCH₃ CH₂CH₃  881 S F SCH₃ CH₂CH₃  882 S Cl SCH₃ CH₂CH₃  883 S Br SCH₃ CH₂CH₃  884 S NO₂ SCH₃ CH₂CH₃  885 S SCH₃ SCH₃ CH₂CH₃  886 S SO₂CH₃ SCH₃ CH₂CH₃  887 S SO₂CH₂CH₃ SCH₃ CH₂CH₃  888 S CH₃ SCH₃ CH₂CH₃  889 S CF₃ SCH₃ CH₂CH₃  890 S OCHF₂ SCH₃ CH₂CH₃  891 SO₂ F SCH₃ CH₂CH₃  892 SO₂ Cl SCH₃ CH₂CH₃  893 SO₂ Br SCH₃ CH₂CH₃  894 SO₂ NO₂ SCH₃ CH₂CH₃  895 SO₂ SCH₃ SCH₃ CH₂CH₃  896 SO₂ SO₂CH₃ SCH₃ CH₂CH₃  897 SO₂ SO₂CH₂CH₃ SCH₃ CH₂CH₃  898 SO₂ CH₃ SCH₃ CH₂CH₃  899 SO₂ CF₃ SCH₃ CH₂CH₃  900 SO₂ OCHF₂ SCH₃ CH₂CH₃  901 bond F Cl CH₃  902 bond Cl Cl CH₃  903 bond Br Cl CH₃  904 bond NO₂ Cl CH₃  905 bond SCH₃ Cl CH₃  906 bond SO₂CH₃ Cl CH₃  907 bond SO₂CH₂CH₃ Cl CH₃  908 bond CH₃ Cl CH₃  909 bond CF₃ Cl CH₃  910 bond OCHF₂ Cl CH₃  911 CH₂ F Cl CH₃  912 CH₂ Cl Cl CH₃  913 CH₂ Br Cl CH₃  914 CH₂ NO₂ Cl CH₃  915 CH₂ SCH₃ Cl CH₃  916 CH₂ SO₂CH₃ Cl CH₃  917 CH₂ SO₂CH₂CH₃ Cl CH₃  918 CH₂ CH₃ Cl CH₃  919 CH₂ CF₃ Cl CH₃  920 CH₂ OCHF₂ Cl CH₃  921 O F Cl CH₃  922 O Cl Cl CH₃  923 O Br Cl CH₃  924 O NO₂ Cl CH₃  925 O SCH₃ Cl CH₃  926 O SO₂CH₃ Cl CH₃  927 O SO₂CH₂CH₃ Cl CH₃  928 O CH₃ Cl CH₃  929 O CF₃ Cl CH₃  930 O OCHF₂ Cl CH₃  931 S F Cl CH₃  932 S Cl Cl CH₃  933 S Br Cl CH₃  934 S NO₂ Cl CH₃  935 S SCH₃ Cl CH₃  936 S SO₂CH₃ Cl CH₃  937 S SO₂CH₂CH₃ Cl CH₃  938 S CH₃ Cl CH₃  939 S CF₃ Cl CH₃  940 S OCHF₂ Cl CH₃  941 SO₂ F Cl CH₃  942 SO₂ Cl Cl CH₃  943 SO₂ Br Cl CH₃  944 SO₂ NO₂ Cl CH₃  945 SO₂ SCH₃ Cl CH₃  946 SO₂ SO₂CH₃ Cl CH₃  947 SO₂ SO₂CH₂CH₃ Cl CH₃  948 SO₂ CH₃ Cl CH₃  949 SO₂ CF₃ Cl CH₃  950 SO₂ OCHF₂ Cl CH₃  951 bond F Cl CH₂CH₃  952 bond Cl Cl CH₂CH₃  953 bond Br Cl CH₂CH₃  954 bond NO₂ Cl CH₂CH₃  955 bond SCH₃ Cl CH₂CH₃  956 bond SO₂CH₃ Cl CH₂CH₃  957 bond SO₂CH₂CH₃ Cl CH₂CH₃  958 bond CH₃ Cl CH₂CH₃  959 bond CF₃ Cl CH₂CH₃  960 bond OCHF₂ Cl CH₂CH₃  961 CH₂ F Cl CH₂CH₃  962 CH₂ Cl Cl CH₂CH₃  963 CH₂ Br Cl CH₂CH₃  964 CH₂ NO₂ Cl CH₂CH₃  965 CH₂ SCH₃ Cl CH₂CH₃  966 CH₂ SO₂CH₃ Cl CH₂CH₃  967 CH₂ SO₂CH₂CH₃ Cl CH₂CH₃  968 CH₂ CH₃ Cl CH₂CH₃  969 CH₂ CF₃ Cl CH₂CH₃  970 CH₂ OCHF₂ Cl CH₂CH₃  971 O F Cl CH₂CH₃  972 O Cl Cl CH₂CH₃  973 O Br Cl CH₂CH₃  974 O NO₂ Cl CH₂CH₃  975 O SCH₃ Cl CH₂CH₃  976 O SO₂CH₃ Cl CH₂CH₃  977 O SO₂CH₂CH₃ Cl CH₂CH₃  978 O CH₃ Cl CH₂CH₃  979 O CF₃ Cl CH₂CH₃  980 O OCHF₂ Cl CH₂CH₃  981 S F Cl CH₂CH₃  982 S Cl Cl CH₂CH₃  983 S Br Cl CH₂CH₃  984 S NO₂ Cl CH₂CH₃  985 S SCH₃ Cl CH₂CH₃  986 S SO₂CH₃ Cl CH₂CH₃  987 S SO₂CH₂CH₃ Cl CH₂CH₃  988 S CH₃ Cl CH₂CH₃  989 S CF₃ Cl CH₂CH₃  990 S OCHF₂ Cl CH₂CH₃  991 SO₂ F Cl CH₂CH₃  992 SO₂ Cl Cl CH₂CH₃  993 SO₂ Br Cl CH₂CH₃  994 SO₂ NO₂ Cl CH₂CH₃  995 SO₂ SCH₃ Cl CH₂CH₃  996 SO₂ SO₂CH₃ Cl CH₂CH₃  997 SO₂ SO₂CH₂CH₃ Cl CH₂CH₃  998 SO₂ CH₃ Cl CH₂CH₃  999 SO₂ CF₃ Cl CH₂CH₃ 1000 SO₂ OCHF₂ Cl CH₂CH₃ 1001 bond F OH CH(CH₃)₂ 1002 bond Cl OH CH(CH₃)₂ 1003 bond Br OH CH(CH₃)₂ 1004 bond NO₂ OH CH(CH₃)₂ 1005 bond SCH₃ OH CH(CH₃)₂ 1006 bond SO₂CH₃ OH CH(CH₃)₂ 1007 bond SO₂CH₂CH₃ OH CH(CH₃)₂ 1008 bond CH₃ OH CH(CH₃)₂ 1009 bond CF₃ OH CH(CH₃)₂ 1010 bond OCHF₂ OH CH(CH₃)₂ 1011 CH₂ F OH CH(CH₃)₂ 1012 CH₂ Cl OH CH(CH₃)₂ 1013 CH₂ Br OH CH(CH₃)₂ 1014 CH₂ NO₂ OH CH(CH₃)₂ 1015 CH₂ SCH₃ OH CH(CH₃)₂ 1016 CH₂ SO₂CH₃ OH CH(CH₃)₂ 1017 CH₂ SO₂CH₂CH₃ OH CH(CH₃)₂ 1018 CH₂ CH₃ OH CH(CH₃)₂ 1019 CH₂ CF₃ OH CH(CH₃)₂ 1020 CH₂ OCHF₂ OH CH(CH₃)₂ 1021 O F OH CH(CH₃)₂ 1022 O Cl OH CH(CH₃)₂ 1023 O Br OH CH(CH₃)₂ 1024 O NO₂ OH CH(CH₃)₂ 1025 O SCH₃ OH CH(CH₃)₂ 1026 O SO₂CH₃ OH CH(CH₃)₂ 1027 O SO₂CH₂CH₃ OH CH(CH₃)₂ 1028 O CH₃ OH CH(CH₃)₂ 1029 O CF₃ OH CH(CH₃)₂ 1030 O OCHF₂ OH CH(CH₃)₂ 1031 S F OH CH(CH₃)₂ 1032 S Cl OH CH(CH₃)₂ 1033 S Br OH CH(CH₃)₂ 1034 S NO₂ OH CH(CH₃)₂ 1035 S SCH₃ OH CH(CH₃)₂ 1036 S SO₂CH₃ OH CH(CH₃)₂ 1037 S SO₂CH₂CH₃ OH CH(CH₃)₂ 1038 S CH₃ OH CH(CH₃)₂ 1039 S CF₃ OH CH(CH₃)₂ 1040 S OCHF₂ OH CH(CH₃)₂ 1041 SO₂ F OH CH(CH₃)₂ 1042 SO₂ Cl OH CH(CH₃)₂ 1043 SO₂ Br OH CH(CH₃)₂ 1044 SO₂ NO₂ OH CH(CH₃)₂ 1045 SO₂ SCH₃ OH CH(CH₃)₂ 1046 SO₂ SO₂CH₃ OH CH(CH₃)₂ 1047 SO₂ SO₂CH₂CH₃ OH CH(CH₃)₂ 1048 SO₂ CH₃ OH CH(CH₃)₂ 1049 SO₂ CF₃ OH CH(CH₃)₂ 1050 SO₂ OCHF₂ OH CH(CH₃)₂ 1051 bond F OH C(CH₃)₃ 1052 bond Cl OH C(CH₃)₃ 1053 bond Br OH C(CH₃)₃ 1054 bond NO₂ OH C(CH₃)₃ 1055 bond SCH₃ OH C(CH₃)₃ 1056 bond SO₂CH₃ OH C(CH₃)₃ 1057 bond SO₂CH₂CH₃ OH C(CH₃)₃ 1058 bond CH₃ OH C(CH₃)₃ 1059 bond CF₃ OH C(CH₃)₃ 1060 bond OCHF₂ OH C(CH₃)₃ 1061 CH₂ F OH C(CH₃)₃ 1062 CH₂ Cl OH C(CH₃)₃ 1063 CH₂ Br OH C(CH₃)₃ 1064 CH₂ NO₂ OH C(CH₃)₃ 1065 CH₂ SCH₃ OH C(CH₃)₃ 1066 CH₂ SO₂CH₃ OH C(CH₃)₃ 1067 CH₂ SO₂CH₂CH₃ OH C(CH₃)₃ 1068 CH₂ CH₃ OH C(CH₃)₃ 1069 CH₂ CF₃ OH C(CH₃)₃ 1070 CH₂ OCHF₂ OH C(CH₃)₃ 1071 O F OH C(CH₃)₃ 1072 O Cl OH C(CH₃)₃ 1073 O Br OH C(CH₃)₃ 1074 O NO₂ OH C(CH₃)₃ 1075 O SCH₃ OH C(CH₃)₃ 1076 O SO₂CH₃ OH C(CH₃)₃ 1077 O SO₂CH₂CH₃ OH C(CH₃)₃ 1078 O CH₃ OH C(CH₃)₃ 1079 O CF₃ OH C(CH₃)₃ 1080 O OCHF₂ OH C(CH₃)₃ 1081 S F OH C(CH₃)₃ 1082 S Cl OH C(CH₃)₃ 1083 S Br OH C(CH₃)₃ 1084 S NO₂ OH C(CH₃)₃ 1085 S SCH₃ OH C(CH₃)₃ 1086 S SO₂CH₃ OH C(CH₃)₃ 1087 S SO₂CH₂CH₃ OH C(CH₃)₃ 1088 S CH₃ OH C(CH₃)₃ 1089 S CF₃ OH C(CH₃)₃ 1090 S OCHF₂ OH C(CH₃)₃ 1091 SO₂ F OH C(CH₃)₃ 1092 SO₂ Cl OH C(CH₃)₃ 1093 SO₂ Br OH C(CH₃)₃ 1094 SO₂ NO₂ OH C(CH₃)₃ 1095 SO₂ SCH₃ OH C(CH₃)₃ 1096 SO₂ SO₂CH₃ OH C(CH₃)₃ 1097 SO₂ SO₂CH₂CH₃ OH C(CH₃)₃ 1098 SO₂ CH₃ OH C(CH₃)₃ 1099 SO₂ CF₃ OH C(CH₃)₃ 1100 SO₂ OCHF₂ OH C(CH₃)₃ 1101 bond F OCOC₆H₅ CH(CH₃)₂ 1102 bond Cl OCOC₆H₅ CH(CH₃)₂ 1103 bond Br OCOC₆H₅ CH(CH₃)₂ 1104 bond NO₂ OCOC₆H₅ CH(CH₃)₂ 1105 bond SCH₃ OCOC₆H₅ CH(CH₃)₂ 1106 bond SO₂CH₃ OCOC₆H₅ CH(CH₃)₂ 1107 bond SO₂CH₂CH₃ OCOC₆H₅ CH(CH₃)₂ 1108 bond CH₃ OCOC₆H₅ CH(CH₃)₂ 1109 bond CF₃ OCOC₆H₅ CH(CH₃)₂ 1110 bond OCHF₂ OCOC₆H₅ CH(CH₃)₂ 1111 CH₂ F OCOC₆H₅ CH(CH₃)₂ 1112 CH₂ Cl OCOC₆H₅ CH(CH₃)₂ 1113 CH₂ Br OCOC₆H₅ CH(CH₃)₂ 1114 CH₂ NO₂ OCOC₆H₅ CH(CH₃)₂ 1115 CH₂ SCH₃ OCOC₆H₅ CH(CH₃)₂ 1116 CH₂ SO₂CH₃ OCOC₆H₅ CH(CH₃)₂ 1117 CH₂ SO₂CH₂CH₃ OCOC₆H₅ CH(CH₃)₂ 1118 CH₂ CH₃ OCOC₆H₅ CH(CH₃)₂ 1119 CH₂ CF₃ OCOC₆H₅ CH(CH₃)₂ 1120 CH₂ OCHF₂ OCOC₆H₅ CH(CH₃)₂ 1121 O F OCOC₆H₅ CH(CH₃)₂ 1122 O Cl OCOC₆H₅ CH(CH₃)₂ 1123 O Br OCOC₆H₅ CH(CH₃)₂ 1124 O NO₂ OCOC₆H₅ CH(CH₃)₂ 1125 O SCH₃ OCOC₆H₅ CH(CH₃)₂ 1126 O SO₂CH₃ OCOC₆H₅ CH(CH₃)₂ 1127 O SO₂CH₂CH₃ OCOC₆H₅ CH(CH₃)₂ 1128 O CH₃ OCOC₆H₅ CH(CH₃)₂ 1129 O CF₃ OCOC₆H₅ CH(CH₃)₂ 1130 O OCHF₂ OCOC₆H₅ CH(CH₃)₂ 1131 S F OCOC₆H₅ CH(CH₃)₂ 1132 S Cl OCOC₆H₅ CH(CH₃)₂ 1133 S Br OCOC₆H₅ CH(CH₃)₂ 1134 S NO₂ OCOC₆H₅ CH(CH₃)₂ 1135 S SCH₃ OCOC₆H₅ CH(CH₃)₂ 1136 S SO₂CH₃ OCOC₆H₅ CH(CH₃)₂ 1137 S SO₂CH₂CH₃ OCOC₆H₅ CH(CH₃)₂ 1138 S CH₃ OCOC₆H₅ CH(CH₃)₂ 1139 S CF₃ OCOC₆H₅ CH(CH₃)₂ 1140 S OCHF₂ OCOC₆H₅ CH(CH₃)₂ 1141 SO₂ F OCOC₆H₅ CH(CH₃)₂ 1142 SO₂ Cl OCOC₆H₅ CH(CH₃)₂ 1143 SO₂ Br OCOC₆H₅ CH(CH₃)₂ 1144 SO₂ NO₂ OCOC₆H₅ CH(CH₃)₂ 1145 SO₂ SCH₃ OCOC₆H₅ CH(CH₃)₂ 1146 SO₂ SO₂CH₃ OCOC₆H₅ CH(CH₃)₂ 1147 SO₂ SO₂CH₂CH₃ OCOC₆H₅ CH(CH₃)₂ 1148 SO₂ CH₃ OCOC₆H₅ CH(CH₃)₂ 1149 SO₂ CF₃ OCOC₆H₅ CH(CH₃)₂ 1150 SO₂ OCHF₂ OCOC₆H₅ CH(CH₃)₂ 1151 bond F OCOC₆H₅ C(CH₃)₃ 1152 bond Cl OCOC₆H₅ C(CH₃)₃ 1153 bond Br OCOC₆H₅ C(CH₃)₃ 1154 bond NO₂ OCOC₆H₅ C(CH₃)₃ 1155 bond SCH₃ OCOC₆H₅ C(CH₃)₃ 1156 bond SO₂CH₃ OCOC₆H₅ C(CH₃)₃ 1157 bond SO₂CH₂CH₃ OCOC₆H₅ C(CH₃)₃ 1158 bond CH₃ OCOC₆H₅ C(CH₃)₃ 1159 bond CF₃ OCOC₆H₅ C(CH₃)₃ 1160 bond OCHF₂ OCOC₆H₅ C(CH₃)₃ 1161 CH₂ F OCOC₆H₅ C(CH₃)₃ 1162 CH₂ Cl OCOC₆H₅ C(CH₃)₃ 1163 CH₂ Br OCOC₆H₅ C(CH₃)₃ 1164 CH₂ NO₂ OCOC₆H₅ C(CH₃)₃ 1165 CH₂ SCH₃ OCOC₆H₅ C(CH₃)₃ 1166 CH₂ SO₂CH₃ OCOC₆H₅ C(CH₃)₃ 1167 CH₂ SO₂CH₂CH₃ OCOC₆H₅ C(CH₃)₃ 1168 CH₂ CH₃ OCOC₆H₅ C(CH₃)₃ 1169 CH₂ CF₃ OCOC₆H₅ C(CH₃)₃ 1170 CH₂ OCHF₂ OCOC₆H₅ C(CH₃)₃ 1171 O F OCOC₆H₅ C(CH₃)₃ 1172 O Cl OCOC₆H₅ C(CH₃)₃ 1173 O Br OCOC₆H₅ C(CH₃)₃ 1174 O NO₂ OCOC₆H₅ C(CH₃)₃ 1175 O SCH₃ OCOC₆H₅ C(CH₃)₃ 1176 O SO₂CH₃ OCOC₆H₅ C(CH₃)₃ 1177 O SO₂CH₂CH₃ OCOC₆H₅ C(CH₃)₃ 1178 O CH₃ OCOC₆H₅ C(CH₃)₃ 1179 O CF₃ OCOC₆H₅ C(CH₃)₃ 1180 O OCHF₂ OCOC₆H₅ C(CH₃)₃ 1181 S F OCOC₆H₅ C(CH₃)₃ 1182 S Cl OCOC₆H₅ C(CH₃)₃ 1183 S Br OCOC₆H₅ C(CH₃)₃ 1184 S NO₂ OCOC₆H₅ C(CH₃)₃ 1185 S SCH₃ OCOC₆H₅ C(CH₃)₃ 1186 S SO₂CH₃ OCOC₆H₅ C(CH₃)₃ 1187 S SO₂CH₂CH₃ OCOC₆H₅ C(CH₃)₃ 1188 S CH₃ OCOC₆H₅ C(CH₃)₃ 1189 S CF₃ OCOC₆H₅ C(CH₃)₃ 1190 S OCHF₂ OCOC₆H₅ C(CH₃)₃ 1191 SO₂ F OCOC₆H₅ C(CH₃)₃ 1192 SO₂ Cl OCOC₆H₅ C(CH₃)₃ 1193 SO₂ Br OCOC₆H₅ C(CH₃)₃ 1194 SO₂ NO₂ OCOC₆H₅ C(CH₃)₃ 1195 SO₂ SCH₃ OCOC₆H₅ C(CH₃)₃ 1196 SO₂ SO₂CH₃ OCOC₆H₅ C(CH₃)₃ 1197 SO₂ SO₂CH₂CH₃ OCOC₆H₅ C(CH₃)₃ 1198 SO₂ CH₃ OCOC₆H₅ C(CH₃)₃ 1199 SO₂ CF₃ OCOC₆H₅ C(CH₃)₃ 1200 SO₂ OCHF₂ OCOC₆H₅ C(CH₃)₃ 1201 bond F OCOC(CH₃)₃ CH(CH₃)₂ 1202 bond Cl OCOC(CH₃)₃ CH(CH₃)₂ 1203 bond Br OCOC(CH₃)₃ CH(CH₃)₂ 1204 bond NO₂ OCOC(CH₃)₃ CH(CH₃)₂ 1205 bond SCH₃ OCOC(CH₃)₃ CH(CH₃)₂ 1206 bond SO₂CH₃ OCOC(CH₃)₃ CH(CH₃)₂ 1207 bond SO₂CH₂CH₃ OCOC(CH₃)₃ CH(CH₃)₂ 1208 bond CH₃ OCOC(CH₃)₃ CH(CH₃)₂ 1209 bond CF₃ OCOC(CH₃)₃ CH(CH₃)₂ 1210 bond OCHF₂ OCOC(CH₃)₃ CH(CH₃)₂ 1211 CH₂ F OCOC(CH₃)₃ CH(CH₃)₂ 1212 CH₂ Cl OCOC(CH₃)₃ CH(CH₃)₂ 1213 CH₂ Br OCOC(CH₃)₃ CH(CH₃)₂ 1214 CH₂ NO₂ OCOC(CH₃)₃ CH(CH₃)₂ 1215 CH₂ SCH₃ OCOC(CH₃)₃ CH(CH₃)₂ 1216 CH₂ SO₂CH₃ OCOC(CH₃)₃ CH(CH₃)₂ 1217 CH₂ SO₂CH₂CH₃ OCOC(CH₃)₃ CH(CH₃)₂ 1218 CH₂ CH₃ OCOC(CH₃)₃ CH(CH₃)₂ 1219 CH₂ CF₃ OCOC(CH₃)₃ CH(CH₃)₂ 1220 CH₂ OCHF₂ OCOC(CH₃)₃ CH(CH₃)₂ 1221 O F OCOC(CH₃)₃ CH(CH₃)₂ 1222 O Cl OCOC(CH₃)₃ CH(CH₃)₂ 1223 O Br OCOC(CH₃)₃ CH(CH₃)₂ 1224 O NO₂ OCOC(CH₃)₃ CH(CH₃)₂ 1225 O SCH₃ OCOC(CH₃)₃ CH(CH₃)₂ 1226 O SO₂CH₃ OCOC(CH₃)₃ CH(CH₃)₂ 1227 O SO₂CH₂CH₃ OCOC(CH₃)₃ CH(CH₃)₂ 1228 O CH₃ OCOC(CH₃)₃ CH(CH₃)₂ 1229 O CF₃ OCOC(CH₃)₃ CH(CH₃)₂ 1230 O OCHF₂ OCOC(CH₃)₃ CH(CH₃)₂ 1231 S F OCOC(CH₃)₃ CH(CH₃)₂ 1232 S Cl OCOC(CH₃)₃ CH(CH₃)₂ 1233 S Br OCOC(CH₃)₃ CH(CH₃)₂ 1234 S NO₂ OCOC(CH₃)₃ CH(CH₃)₂ 1235 S SCH₃ OCOC(CH₃)₃ CH(CH₃)₂ 1236 S SO₂CH₃ OCOC(CH₃)₃ CH(CH₃)₂ 1237 S SO₂CH₂CH₃ OCOC(CH₃)₃ CH(CH₃)₂ 1238 S CH₃ OCOC(CH₃)₃ CH(CH₃)₂ 1239 S CF₃ OCOC(CH₃)₃ CH(CH₃)₂ 1240 S OCHF₂ OCOC(CH₃)₃ CH(CH₃)₂ 1241 SO₂ F OCOC(CH₃)₃ CH(CH₃)₂ 1242 SO₂ Cl OCOC(CH₃)₃ CH(CH₃)₂ 1243 SO₂ Br OCOC(CH₃)₃ CH(CH₃)₂ 1244 SO₂ NO₂ OCOC(CH₃)₃ CH(CH₃)₂ 1245 SO₂ SCH₃ OCOC(CH₃)₃ CH(CH₃)₂ 1246 SO₂ SO₂CH₃ OCOC(CH₃)₃ CH(CH₃)₂ 1247 SO₂ SO₂CH₂CH₃ OCOC(CH₃)₃ CH(CH₃)₂ 1248 SO₂ CH₃ OCOC(CH₃)₃ CH(CH₃)₂ 1249 SO₂ CF₃ OCOC(CH₃)₃ CH(CH₃)₂ 1250 SO₂ OCHF₂ OCOC(CH₃)₃ CH(CH₃)₂ 1251 bond F OCOC(CH₃)₃ C(CH₃)₃ 1252 bond Cl OCOC(CH₃)₃ C(CH₃)₃ 1253 bond Br OCOC(CH₃)₃ C(CH₃)₃ 1254 bond NO₂ OCOC(CH₃)₃ C(CH₃)₃ 1255 bond SCH₃ OCOC(CH₃)₃ C(CH₃)₃ 1256 bond SO₂CH₃ OCOC(CH₃)₃ C(CH₃)₃ 1257 bond SO₂CH₂CH₃ OCOC(CH₃)₃ C(CH₃)₃ 1258 bond CH₃ OCOC(CH₃)₃ C(CH₃)₃ 1259 bond CF₃ OCOC(CH₃)₃ C(CH₃)₃ 1260 bond OCHF₂ OCOC(CH₃)₃ C(CH₃)₃ 1261 CH₂ F OCOC(CH₃)₃ C(CH₃)₃ 1262 CH₂ Cl OCOC(CH₃)₃ C(CH₃)₃ 1263 CH₂ Br OCOC(CH₃)₃ C(CH₃)₃ 1264 CH₂ NO₂ OCOC(CH₃)₃ C(CH₃)₃ 1265 CH₂ SCH₃ OCOC(CH₃)₃ C(CH₃)₃ 1266 CH₂ SO₂CH₃ OCOC(CH₃)₃ C(CH₃)₃ 1267 CH₂ SO₂CH₂CH₃ OCOC(CH₃)₃ C(CH₃)₃ 1268 CH₂ CH₃ OCOC(CH₃)₃ C(CH₃)₃ 1269 CH₂ CF₃ OCOC(CH₃)₃ C(CH₃)₃ 1270 CH₂ OCHF₂ OCOC(CH₃)₃ C(CH₃)₃ 1271 O F OCOC(CH₃)₃ C(CH₃)₃ 1272 O Cl OCOC(CH₃)₃ C(CH₃)₃ 1273 O Br OCOC(CH₃)₃ C(CH₃)₃ 1274 O NO₂ OCOC(CH₃)₃ C(CH₃)₃ 1275 O SCH₃ OCOC(CH₃)₃ C(CH₃)₃ 1276 O SO₂CH₃ OCOC(CH₃)₃ C(CH₃)₃ 1277 O SO₂CH₂CH₃ OCOC(CH₃)₃ C(CH₃)₃ 1278 O CH₃ OCOC(CH₃)₃ C(CH₃)₃ 1279 O CF₃ OCOC(CH₃)₃ C(CH₃)₃ 1280 O OCHF₂ OCOC(CH₃)₃ C(CH₃)₃ 1281 S F OCOC(CH₃)₃ C(CH₃)₃ 1282 S Cl OCOC(CH₃)₃ C(CH₃)₃ 1283 S Br OCOC(CH₃)₃ C(CH₃)₃ 1284 S NO₂ OCOC(CH₃)₃ C(CH₃)₃ 1285 S SCH₃ OCOC(CH₃)₃ C(CH₃)₃ 1286 S SO₂CH₃ OCOC(CH₃)₃ C(CH₃)₃ 1287 S SO₂CH₂CH₃ OCOC(CH₃)₃ C(CH₃)₃ 1288 S CH₃ OCOC(CH₃)₃ C(CH₃)₃ 1289 S CF₃ OCOC(CH₃)₃ C(CH₃)₃ 1290 S OCHF₂ OCOC(CH₃)₃ C(CH₃)₃ 1291 SO₂ F OCOC(CH₃)₃ C(CH₃)₃ 1292 SO₂ Cl OCOC(CH₃)₃ C(CH₃)₃ 1293 SO₂ Br OCOC(CH₃)₃ C(CH₃)₃ 1294 SO₂ NO₂ OCOC(CH₃)₃ C(CH₃)₃ 1295 SO₂ SCH₃ OCOC(CH₃)₃ C(CH₃)₃ 1296 SO₂ SO₂CH₃ OCOC(CH₃)₃ C(CH₃)₃ 1297 SO₂ SO₂CH₂CH₃ OCOC(CH₃)₃ C(CH₃)₃ 1298 SO₂ CH₃ OCOC(CH₃)₃ C(CH₃)₃ 1299 SO₂ CF₃ OCOC(CH₃)₃ C(CH₃)₃ 1300 SO₂ OCHF₂ OCOC(CH₃)₃ C(CH₃)₃ 1301 bond F OCOSCH₃ CH(CH₃)₂ 1302 bond Cl OCOSCH₃ CH(CH₃)₂ 1303 bond Br OCOSCH₃ CH(CH₃)₂ 1304 bond NO₂ OCOSCH₃ CH(CH₃)₂ 1305 bond SCH₃ OCOSCH₃ CH(CH₃)₂ 1306 bond SO₂CH₃ OCOSCH₃ CH(CH₃)₂ 1307 bond SO₂CH₂CH₃ OCOSCH₃ CH(CH₃)₂ 1308 bond CH₃ OCOSCH₃ CH(CH₃)₂ 1309 bond CF₃ OCOSCH₃ CH(CH₃)₂ 1310 bond OCHF₂ OCOSCH₃ CH(CH₃)₂ 1311 CH₂ F OCOSCH₃ CH(CH₃)₂ 1312 CH₂ Cl OCOSCH₃ CH(CH₃)₂ 1313 CH₂ Br OCOSCH₃ CH(CH₃)₂ 1314 CH₂ NO₂ OCOSCH₃ CH(CH₃)₂ 1315 CH₂ SCH₃ OCOSCH₃ CH(CH₃)₂ 1316 CH₂ SO₂CH₃ OCOSCH₃ CH(CH₃)₂ 1317 CH₂ SO₂CH₂CH₃ OCOSCH₃ CH(CH₃)₂ 1318 CH₂ CH₃ OCOSCH₃ CH(CH₃)₂ 1319 CH₂ CF₃ OCOSCH₃ CH(CH₃)₂ 1320 CH₂ OCHF₂ OCOSCH₃ CH(CH₃)₂ 1321 O F OCOSCH₃ CH(CH₃)₂ 1322 O Cl OCOSCH₃ CH(CH₃)₂ 1323 O Br OCOSCH₃ CH(CH₃)₂ 1324 O NO₂ OCOSCH₃ CH(CH₃)₂ 1325 O SCH₃ OCOSCH₃ CH(CH₃)₂ 1326 O SO₂CH₃ OCOSCH₃ CH(CH₃)₂ 1327 O SO₂CH₂CH₃ OCOSCH₃ CH(CH₃)₂ 1328 O CH₃ OCOSCH₃ CH(CH₃)₂ 1329 O CF₃ OCOSCH₃ CH(CH₃)₂ 1330 O OCHF₂ OCOSCH₃ CH(CH₃)₂ 1331 S F OCOSCH₃ CH(CH₃)₂ 1332 S Cl OCOSCH₃ CH(CH₃)₂ 1333 S Br OCOSCH₃ CH(CH₃)₂ 1334 S NO₂ OCOSCH₃ CH(CH₃)₂ 1335 S SCH₃ OCOSCH₃ CH(CH₃)₂ 1336 S SO₂CH₃ OCOSCH₃ CH(CH₃)₂ 1337 S SO₂CH₂CH₃ OCOSCH₃ CH(CH₃)₂ 1338 S CH₃ OCOSCH₃ CH(CH₃)₂ 1339 S CF₃ OCOSCH₃ CH(CH₃)₂ 1340 S OCHF₂ OCOSCH₃ CH(CH₃)₂ 1341 SO₂ F OCOSCH₃ CH(CH₃)₂ 1342 SO₂ Cl OCOSCH₃ CH(CH₃)₂ 1343 SO₂ Br OCOSCH₃ CH(CH₃)₂ 1344 SO₂ NO₂ OCOSCH₃ CH(CH₃)₂ 1345 SO₂ SCH₃ OCOSCH₃ CH(CH₃)₂ 1346 SO₂ SO₂CH₃ OCOSCH₃ CH(CH₃)₂ 1347 SO₂ SO₂CH₂CH₃ OCOSCH₃ CH(CH₃)₂ 1348 SO₂ CH₃ OCOSCH₃ CH(CH₃)₂ 1349 SO₂ CF₃ OCOSCH₃ CH(CH₃)₂ 1350 SO₂ OCHF₂ OCOSCH₃ CH(CH₃)₂ 1351 bond F OCOSCH₃ C(CH₃)₃ 1352 bond Cl OCOSCH₃ C(CH₃)₃ 1353 bond Br OCOSCH₃ C(CH₃)₃ 1354 bond NO₂ OCOSCH₃ C(CH₃)₃ 1355 bond SCH₃ OCOSCH₃ C(CH₃)₃ 1356 bond SO₂CH₃ OCOSCH₃ C(CH₃)₃ 1357 bond SO₂CH₂CH₃ OCOSCH₃ C(CH₃)₃ 1358 bond CH₃ OCOSCH₃ C(CH₃)₃ 1359 bond CF₃ OCOSCH₃ C(CH₃)₃ 1360 bond OCHF₂ OCOSCH₃ C(CH₃)₃ 1361 CH₂ F OCOSCH₃ C(CH₃)₃ 1362 CH₂ Cl OCOSCH₃ C(CH₃)₃ 1363 CH₂ Br OCOSCH₃ C(CH₃)₃ 1364 CH₂ NO₂ OCOSCH₃ C(CH₃)₃ 1365 CH₂ SCH₃ OCOSCH₃ C(CH₃)₃ 1366 CH₂ SO₂CH₃ OCOSCH₃ C(CH₃)₃ 1367 CH₂ SO₂CH₂CH₃ OCOSCH₃ C(CH₃)₃ 1368 CH₂ CH₃ OCOSCH₃ C(CH₃)₃ 1369 CH₂ CF₃ OCOSCH₃ C(CH₃)₃ 1370 CH₂ OCHF₂ OCOSCH₃ C(CH₃)₃ 1371 O F OCOSCH₃ C(CH₃)₃ 1372 O Cl OCOSCH₃ C(CH₃)₃ 1373 O Br OCOSCH₃ C(CH₃)₃ 1374 O NO₂ OCOSCH₃ C(CH₃)₃ 1375 O SCH₃ OCOSCH₃ C(CH₃)₃ 1376 O SO₂CH₃ OCOSCH₃ C(CH₃)₃ 1377 O SO₂CH₂CH₃ OCOSCH₃ C(CH₃)₃ 1378 O CH₃ OCOSCH₃ C(CH₃)₃ 1379 O CF₃ OCOSCH₃ C(CH₃)₃ 1380 O OCHF₂ OCOSCH₃ C(CH₃)₃ 1381 S F OCOSCH₃ C(CH₃)₃ 1382 S Cl OCOSCH₃ C(CH₃)₃ 1383 S Br OCOSCH₃ C(CH₃)₃ 1384 S NO₂ OCOSCH₃ C(CH₃)₃ 1385 S SCH₃ OCOSCH₃ C(CH₃)₃ 1386 S SO₂CH₃ OCOSCH₃ C(CH₃)₃ 1387 S SO₂CH₂CH₃ OCOSCH₃ C(CH₃)₃ 1388 S CH₃ OCOSCH₃ C(CH₃)₃ 1389 S CF₃ OCOSCH₃ C(CH₃)₃ 1390 S OCHF₂ OCOSCH₃ C(CH₃)₃ 1391 SO₂ F OCOSCH₃ C(CH₃)₃ 1392 SO₂ Cl OCOSCH₃ C(CH₃)₃ 1393 SO₂ Br OCOSCH₃ C(CH₃)₃ 1394 SO₂ NO₂ OCOSCH₃ C(CH₃)₃ 1395 SO₂ SCH₃ OCOSCH₃ C(CH₃)₃ 1396 SO₂ SO₂CH₃ OCOSCH₃ C(CH₃)₃ 1397 SO₂ SO₂CH₂CH₃ OCOSCH₃ C(CH₃)₃ 1398 SO₂ CH₃ OCOSCH₃ C(CH₃)₃ 1399 SO₂ CF₃ OCOSCH₃ C(CH₃)₃ 1400 SO₂ OCHF₂ OCOSCH₃ C(CH₃)₃ 1401 bond F OCH₃ CH(CH₃)₂ 1402 bond Cl OCH₃ CH(CH₃)₂ 1403 bond Br OCH₃ CH(CH₃)₂ 1404 bond NO₂ OCH₃ CH(CH₃)₂ 1405 bond SCH₃ OCH₃ CH(CH₃)₂ 1406 bond SO₂CH₃ OCH₃ CH(CH₃)₂ 1407 bond SO₂CH₂CH₃ OCH₃ CH(CH₃)₂ 1408 bond CH₃ OCH₃ CH(CH₃)₂ 1409 bond CF₃ OCH₃ CH(CH₃)₂ 1410 bond OCHF₂ OCH₃ CH(CH₃)₂ 1411 CH₂ F OCH₃ CH(CH₃)₂ 1412 CH₂ Cl OCH₃ CH(CH₃)₂ 1413 CH₂ Br OCH₃ CH(CH₃)₂ 1414 CH₂ NO₂ OCH₃ CH(CH₃)₂ 1415 CH₂ SCH₃ OCH₃ CH(CH₃)₂ 1416 CH₂ SO₂CH₃ OCH₃ CH(CH₃)₂ 1417 CH₂ SO₂CH₂CH₃ OCH₃ CH(CH₃)₂ 1418 CH₂ CH₃ OCH₃ CH(CH₃)₂ 1419 CH₂ CF₃ OCH₃ CH(CH₃)₂ 1420 CH₂ OCHF₂ OCH₃ CH(CH₃)₂ 1421 O F OCH₃ CH(CH₃)₂ 1422 O Cl OCH₃ CH(CH₃)₂ 1423 O Br OCH₃ CH(CH₃)₂ 1424 O NO₂ OCH₃ CH(CH₃)₂ 1425 O SCH₃ OCH₃ CH(CH₃)₂ 1426 O SO₂CH₃ OCH₃ CH(CH₃)₂ 1427 O SO₂CH₂CH₃ OCH₃ CH(CH₃)₂ 1428 O CH₃ OCH₃ CH(CH₃)₂ 1429 O CF₃ OCH₃ CH(CH₃)₂ 1430 O OCHF₂ OCH₃ CH(CH₃)₂ 1431 S F OCH₃ CH(CH₃)₂ 1432 S Cl OCH₃ CH(CH₃)₂ 1433 S Br OCH₃ CH(CH₃)₂ 1434 S NO₂ OCH₃ CH(CH₃)₂ 1435 S SCH₃ OCH₃ CH(CH₃)₂ 1436 S SO₂CH₃ OCH₃ CH(CH₃)₂ 1437 S SO₂CH₂CH₃ OCH₃ CH(CH₃)₂ 1438 S CH₃ OCH₃ CH(CH₃)₂ 1439 S CF₃ OCH₃ CH(CH₃)₂ 1440 S OCHF₂ OCH₃ CH(CH₃)₂ 1441 SO₂ F OCH₃ CH(CH₃)₂ 1442 SO₂ Cl OCH₃ CH(CH₃)₂ 1443 SO₂ Br OCH₃ CH(CH₃)₂ 1444 SO₂ NO₂ OCH₃ CH(CH₃)₂ 1445 SO₂ SCH₃ OCH₃ CH(CH₃)₂ 1446 SO₂ SO₂CH₃ OCH₃ CH(CH₃)₂ 1447 SO₂ SO₂CH₂CH₃ OCH₃ CH(CH₃)₂ 1448 SO₂ CH₃ OCH₃ CH(CH₃)₂ 1449 SO₂ CF₃ OCH₃ CH(CH₃)₂ 1450 SO₂ OCHF₂ OCH₃ CH(CH₃)₂ 1451 bond F OCH₃ C(CH₃)₃ 1452 bond Cl OCH₃ C(CH₃)₃ 1453 bond Br OCH₃ C(CH₃)₃ 1454 bond NO₂ OCH₃ C(CH₃)₃ 1455 bond SCH₃ OCH₃ C(CH₃)₃ 1456 bond SO₂CH₃ OCH₃ C(CH₃)₃ 1457 bond SO₂CH₂CH₃ OCH₃ C(CH₃)₃ 1458 bond CH₃ OCH₃ C(CH₃)₃ 1459 bond CF₃ OCH₃ C(CH₃)₃ 1460 bond OCHF₂ OCH₃ C(CH₃)₃ 1461 CH₂ F OCH₃ C(CH₃)₃ 1462 CH₂ Cl OCH₃ C(CH₃)₃ 1463 CH₂ Br OCH₃ C(CH₃)₃ 1464 CH₂ NO₂ OCH₃ C(CH₃)₃ 1465 CH₂ SCH₃ OCH₃ C(CH₃)₃ 1466 CH₂ SO₂CH₃ OCH₃ C(CH₃)₃ 1467 CH₂ SO₂CH₂CH₃ OCH₃ C(CH₃)₃ 1468 CH₂ CH₃ OCH₃ C(CH₃)₃ 1469 CH₂ CF₃ OCH₃ C(CH₃)₃ 1470 CH₂ OCHF₂ OCH₃ C(CH₃)₃ 1471 O F OCH₃ C(CH₃)₃ 1472 O Cl OCH₃ C(CH₃)₃ 1473 O Br OCH₃ C(CH₃)₃ 1474 O NO₂ OCH₃ C(CH₃)₃ 1475 O SCH₃ OCH₃ C(CH₃)₃ 1476 O SO₂CH₃ OCH₃ C(CH₃)₃ 1477 O SO₂CH₂CH₃ OCH₃ C(CH₃)₃ 1478 O CH₃ OCH₃ C(CH₃)₃ 1479 O CF₃ OCH₃ C(CH₃)₃ 1480 O OCHF₂ OCH₃ C(CH₃)₃ 1481 S F OCH₃ C(CH₃)₃ 1482 S Cl OCH₃ C(CH₃)₃ 1483 S Br OCH₃ C(CH₃)₃ 1484 S NO₂ OCH₃ C(CH₃)₃ 1485 S SCH₃ OCH₃ C(CH₃)₃ 1486 S SO₂CH₃ OCH₃ C(CH₃)₃ 1487 S SO₂CH₂CH₃ OCH₃ C(CH₃)₃ 1488 S CH₃ OCH₃ C(CH₃)₃ 1489 S CF₃ OCH₃ C(CH₃)₃ 1490 S OCHF₂ OCH₃ C(CH₃)₃ 1491 SO₂ F OCH₃ C(CH₃)₃ 1492 SO₂ Cl OCH₃ C(CH₃)₃ 1493 SO₂ Br OCH₃ C(CH₃)₃ 1494 SO₂ NO₂ OCH₃ C(CH₃)₃ 1495 SO₂ SCH₃ OCH₃ C(CH₃)₃ 1496 SO₂ SO₂CH₃ OCH₃ C(CH₃)₃ 1497 SO₂ SO₂CH₂CH₃ OCH₃ C(CH₃)₃ 1498 SO₂ CH₃ OCH₃ C(CH₃)₃ 1499 SO₂ CF₃ OCH₃ C(CH₃)₃ 1500 SO₂ OCHF₂ OCH₃ C(CH₃)₃ 1501 bond F OCH(CH₃)₂ CH(CH₃)₂ 1502 bond Cl OCH(CH₃)₂ CH(CH₃)₂ 1503 bond Br OCH(CH₃)₂ CH(CH₃)₂ 1504 bond NO₂ OCH(CH₃)₂ CH(CH₃)₂ 1505 bond SCH₃ OCH(CH₃)₂ CH(CH₃)₂ 1506 bond SO₂CH₃ OCH(CH₃)₂ CH(CH₃)₂ 1507 bond SO₂CH₂CH₃ OCH(CH₃)₂ CH(CH₃)₂ 1508 bond CH₃ OCH(CH₃)₂ CH(CH₃)₂ 1509 bond CF₃ OCH(CH₃)₂ CH(CH₃)₂ 1510 bond OCHF₂ OCH(CH₃)₂ CH(CH₃)₂ 1511 CH₂ F OCH(CH₃)₂ CH(CH₃)₂ 1512 CH₂ Cl OCH(CH₃)₂ CH(CH₃)₂ 1513 CH₂ Br OCH(CH₃)₂ CH(CH₃)₂ 1514 CH₂ NO₂ OCH(CH₃)₂ CH(CH₃)₂ 1515 CH₂ SCH₃ OCH(CH₃)₂ CH(CH₃)₂ 1516 CH₂ SO₂CH₃ OCH(CH₃)₂ CH(CH₃)₂ 1517 CH₂ SO₂CH₂CH₃ OCH(CH₃)₂ CH(CH₃)₂ 1518 CH₂ CH₃ OCH(CH₃)₂ CH(CH₃)₂ 1519 CH₂ CF₃ OCH(CH₃)₂ CH(CH₃)₂ 1520 CH₂ OCHF₂ OCH(CH₃)₂ CH(CH₃)₂ 1521 O F OCH(CH₃)₂ CH(CH₃)₂ 1522 O Cl OCH(CH₃)₂ CH(CH₃)₂ 1523 O Br OCH(CH₃)₂ CH(CH₃)₂ 1524 O NO₂ OCH(CH₃)₂ CH(CH₃)₂ 1525 O SCH₃ OCH(CH₃)₂ CH(CH₃)₂ 1526 O SO₂CH₃ OCH(CH₃)₂ CH(CH₃)₂ 1527 O SO₂CH₂CH₃ OCH(CH₃)₂ CH(CH₃)₂ 1528 O CH₃ OCH(CH₃)₂ CH(CH₃)₂ 1529 O CF₃ OCH(CH₃)₂ CH(CH₃)₂ 1530 O OCHF₂ OCH(CH₃)₂ CH(CH₃)₂ 1531 S F OCH(CH₃)₂ CH(CH₃)₂ 1532 S Cl OCH(CH₃)₂ CH(CH₃)₂ 1533 S Br OCH(CH₃)₂ CH(CH₃)₂ 1534 S NO₂ OCH(CH₃)₂ CH(CH₃)₂ 1535 S SCH₃ OCH(CH₃)₂ CH(CH₃)₂ 1536 S SO₂CH₃ OCH(CH₃)₂ CH(CH₃)₂ 1537 S SO₂CH₂CH₃ OCH(CH₃)₂ CH(CH₃)₂ 1538 S CH₃ OCH(CH₃)₂ CH(CH₃)₂ 1539 S CF₃ OCH(CH₃)₂ CH(CH₃)₂ 1540 S OCHF₂ OCH(CH₃)₂ CH(CH₃)₂ 1541 SO₂ F OCH(CH₃)₂ CH(CH₃)₂ 1542 SO₂ Cl OCH(CH₃)₂ CH(CH₃)₂ 1543 SO₂ Br OCH(CH₃)₂ CH(CH₃)₂ 1544 SO₂ NO₂ OCH(CH₃)₂ CH(CH₃)₂ 1545 SO₂ SCH₃ OCH(CH₃)₂ CH(CH₃)₂ 1546 SO₂ SO₂CH₃ OCH(CH₃)₂ CH(CH₃)₂ 1547 SO₂ SO₂CH₂CH₃ OCH(CH₃)₂ CH(CH₃)₂ 1548 SO₂ CH₃ OCH(CH₃)₂ CH(CH₃)₂ 1549 SO₂ CF₃ OCH(CH₃)₂ CH(CH₃)₂ 1550 SO₂ OCHF₂ OCH(CH₃)₂ CH(CH₃)₂ 1551 bond F OCH(CH₃)₂ C(CH₃)₃ 1552 bond Cl OCH(CH₃)₂ C(CH₃)₃ 1553 bond Br OCH(CH₃)₂ C(CH₃)₃ 1554 bond NO₂ OCH(CH₃)₂ C(CH₃)₃ 1555 bond SCH₃ OCH(CH₃)₂ C(CH₃)₃ 1556 bond SO₂CH₃ OCH(CH₃)₂ C(CH₃)₃ 1557 bond SO₂CH₂CH₃ OCH(CH₃)₂ C(CH₃)₃ 1558 bond CH₃ OCH(CH₃)₂ C(CH₃)₃ 1559 bond CF₃ OCH(CH₃)₂ C(CH₃)₃ 1560 bond OCHF₂ OCH(CH₃)₂ C(CH₃)₃ 1561 CH₂ F OCH(CH₃)₂ C(CH₃)₃ 1562 CH₂ Cl OCH(CH₃)₂ C(CH₃)₃ 1563 CH₂ Br OCH(CH₃)₂ C(CH₃)₃ 1564 CH₂ NO₂ OCH(CH₃)₂ C(CH₃)₃ 1565 CH₂ SCH₃ OCH(CH₃)₂ C(CH₃)₃ 1566 CH₂ SO₂CH₃ OCH(CH₃)₂ C(CH₃)₃ 1567 CH₂ SO₂CH₂CH₃ OCH(CH₃)₂ C(CH₃)₃ 1568 CH₂ CH₃ OCH(CH₃)₂ C(CH₃)₃ 1569 CH₂ CF₃ OCH(CH₃)₂ C(CH₃)₃ 1570 CH₂ OCHF₂ OCH(CH₃)₂ C(CH₃)₃ 1571 O F OCH(CH₃)₂ C(CH₃)₃ 1572 O Cl OCH(CH₃)₂ C(CH₃)₃ 1573 O Br OCH(CH₃)₂ C(CH₃)₃ 1574 O NO₂ OCH(CH₃)₂ C(CH₃)₃ 1575 O SCH₃ OCH(CH₃)₂ C(CH₃)₃ 1576 O SO₂CH₃ OCH(CH₃)₂ C(CH₃)₃ 1577 O SO₂CH₂CH₃ OCH(CH₃)₂ C(CH₃)₃ 1578 O CH₃ OCH(CH₃)₂ C(CH₃)₃ 1579 O CF₃ OCH(CH₃)₂ C(CH₃)₃ 1580 O OCHF₂ OCH(CH₃)₂ C(CH₃)₃ 1581 S F OCH(CH₃)₂ C(CH₃)₃ 1582 S Cl OCH(CH₃)₂ C(CH₃)₃ 1583 S Br OCH(CH₃)₂ C(CH₃)₃ 1584 S NO₂ OCH(CH₃)₂ C(CH₃)₃ 1585 S SCH₃ OCH(CH₃)₂ C(CH₃)₃ 1586 S SO₂CH₃ OCH(CH₃)₂ C(CH₃)₃ 1587 S SO₂CH₂CH₃ OCH(CH₃)₂ C(CH₃)₃ 1588 S CH₃ OCH(CH₃)₂ C(CH₃)₃ 1589 S CF₃ OCH(CH₃)₂ C(CH₃)₃ 1590 S OCHF₂ OCH(CH₃)₂ C(CH₃)₃ 1591 SO₂ F OCH(CH₃)₂ C(CH₃)₃ 1592 SO₂ Cl OCH(CH₃)₂ C(CH₃)₃ 1593 SO₂ Br OCH(CH₃)₂ C(CH₃)₃ 1594 SO₂ NO₂ OCH(CH₃)₂ C(CH₃)₃ 1595 SO₂ SCH₃ OCH(CH₃)₂ C(CH₃)₃ 1596 SO₂ SO₂CH₃ OCH(CH₃)₂ C(CH₃)₃ 1597 SO₂ SO₂CH₂CH₃ OCH(CH₃)₂ C(CH₃)₃ 1598 SO₂ CH₃ OCH(CH₃)₂ C(CH₃)₃ 1599 SO₂ CF₃ OCH(CH₃)₂ C(CH₃)₃ 1600 SO₂ OCHF₂ OCH(CH₃)₂ C(CH₃)₃ 1601 bond F OCH₂C₆H₅ CH(CH₃)₂ 1602 bond Cl OCH₂C₆H₅ CH(CH₃)₂ 1603 bond Br OCH₂C₆H₅ CH(CH₃)₂ 1604 bond NO₂ OCH₂C₆H₅ CH(CH₃)₂ 1605 bond SCH₃ OCH₂C₆H₅ CH(CH₃)₂ 1606 bond SO₂CH₃ OCH₂C₆H₅ CH(CH₃)₂ 1607 bond SO₂CH₂CH₃ OCH₂C₆H₅ CH(CH₃)₂ 1608 bond CH₃ OCH₂C₆H₅ CH(CH₃)₂ 1609 bond CF₃ OCH₂C₆H₅ CH(CH₃)₂ 1610 bond OCHF₂ OCH₂C₆H₅ CH(CH₃)₂ 1611 CH₂ F OCH₂C₆H₅ CH(CH₃)₂ 1612 CH₂ Cl OCH₂C₆H₅ CH(CH₃)₂ 1613 CH₂ Br OCH₂C₆H₅ CH(CH₃)₂ 1614 CH₂ NO₂ OCH₂C₆H₅ CH(CH₃)₂ 1615 CH₂ SCH₃ OCH₂C₆H₅ CH(CH₃)₂ 1616 CH₂ SO₂CH₃ OCH₂C₆H₅ CH(CH₃)₂ 1617 CH₂ SO₂CH₂CH₃ OCH₂C₆H₅ CH(CH₃)₂ 1618 CH₂ CH₃ OCH₂C₆H₅ CH(CH₃)₂ 1619 CH₂ CF₃ OCH₂C₆H₅ CH(CH₃)₂ 1620 CH₂ OCHF₂ OCH₂C₆H₅ CH(CH₃)₂ 1621 O F OCH₂C₆H₅ CH(CH₃)₂ 1622 O Cl OCH₂C₆H₅ CH(CH₃)₂ 1623 O Br OCH₂C₆H₅ CH(CH₃)₂ 1624 O NO₂ OCH₂C₆H₅ CH(CH₃)₂ 1625 O SCH₃ OCH₂C₆H₅ CH(CH₃)₂ 1626 O SO₂CH₃ OCH₂C₆H₅ CH(CH₃)₂ 1627 O SO₂CH₂CH₃ OCH₂C₆H₅ CH(CH₃)₂ 1628 O CH₃ OCH₂C₆H₅ CH(CH₃)₂ 1629 O CF₃ OCH₂C₆H₅ CH(CH₃)₂ 1630 O OCHF₂ OCH₂C₆H₅ CH(CH₃)₂ 1631 S F OCH₂C₆H₅ CH(CH₃)₂ 1632 S Cl OCH₂C₆H₅ CH(CH₃)₂ 1633 S Br OCH₂C₆H₅ CH(CH₃)₂ 1634 S NO₂ OCH₂C₆H₅ CH(CH₃)₂ 1635 S SCH₃ OCH₂C₆H₅ CH(CH₃)₂ 1636 S SO₂CH₃ OCH₂C₆H₅ CH(CH₃)₂ 1637 S SO₂CH₂CH₃ OCH₂C₆H₅ CH(CH₃)₂ 1638 S CH₃ OCH₂C₆H₅ CH(CH₃)₂ 1639 S CF₃ OCH₂C₆H₅ CH(CH₃)₂ 1640 S OCHF₂ OCH₂C₆H₅ CH(CH₃)₂ 1641 SO₂ F OCH₂C₆H₅ CH(CH₃)₂ 1642 SO₂ Cl OCH₂C₆H₅ CH(CH₃)₂ 1643 SO₂ Br OCH₂C₆H₅ CH(CH₃)₂ 1644 SO₂ NO₂ OCH₂C₆H₅ CH(CH₃)₂ 1645 SO₂ SCH₃ OCH₂C₆H₅ CH(CH₃)₂ 1646 SO₂ SO₂CH₃ OCH₂C₆H₅ CH(CH₃)₂ 1647 SO₂ SO₂CH₂CH₃ OCH₂C₆H₅ CH(CH₃)₂ 1648 SO₂ CH₃ OCH₂C₆H₅ CH(CH₃)₂ 1649 SO₂ CF₃ OCH₂C₆H₅ CH(CH₃)₂ 1650 SO₂ OCHF₂ OCH₂C₆H₅ CH(CH₃)₂ 1651 bond F OCH₂C₆H₅ C(CH₃)₃ 1652 bond Cl OCH₂C₆H₅ C(CH₃)₃ 1653 bond Br OCH₂C₆H₅ C(CH₃)₃ 1654 bond NO₂ OCH₂C₆H₅ C(CH₃)₃ 1655 bond SCH₃ OCH₂C₆H₅ C(CH₃)₃ 1656 bond SO₂CH₃ OCH₂C₆H₅ C(CH₃)₃ 1657 bond SO₂CH₂CH₃ OCH₂C₆H₅ C(CH₃)₃ 1658 bond CH₃ OCH₂C₆H₅ C(CH₃)₃ 1659 bond CF₃ OCH₂C₆H₅ C(CH₃)₃ 1660 bond OCHF₂ OCH₂C₆H₅ C(CH₃)₃ 1661 CH₂ F OCH₂C₆H₅ C(CH₃)₃ 1662 CH₂ Cl OCH₂C₆H₅ C(CH₃)₃ 1663 CH₂ Br OCH₂C₆H₅ C(CH₃)₃ 1664 CH₂ NO₂ OCH₂C₆H₅ C(CH₃)₃ 1665 CH₂ SCH₃ OCH₂C₆H₅ C(CH₃)₃ 1666 CH₂ SO₂CH₃ OCH₂C₆H₅ C(CH₃)₃ 1667 CH₂ SO₂CH₂CH₃ OCH₂C₆H₅ C(CH₃)₃ 1668 CH₂ CH₃ OCH₂C₆H₅ C(CH₃)₃ 1669 CH₂ CF₃ OCH₂C₆H₅ C(CH₃)₃ 1670 CH₂ OCHF₂ OCH₂C₆H₅ C(CH₃)₃ 1671 O F OCH₂C₆H₅ C(CH₃)₃ 1672 O Cl OCH₂C₆H₅ C(CH₃)₃ 1673 O Br OCH₂C₆H₅ C(CH₃)₃ 1674 O NO₂ OCH₂C₆H₅ C(CH₃)₃ 1675 O SCH₃ OCH₂C₆H₅ C(CH₃)₃ 1676 O SO₂CH₃ OCH₂C₆H₅ C(CH₃)₃ 1677 O SO₂CH₂CH₃ OCH₂C₆H₅ C(CH₃)₃ 1678 O CH₃ OCH₂C₆H₅ C(CH₃)₃ 1679 O CF₃ OCH₂C₆H₅ C(CH₃)₃ 1680 O OCHF₂ OCH₂C₆H₅ C(CH₃)₃ 1681 S F OCH₂C₆H₅ C(CH₃)₃ 1682 S Cl OCH₂C₆H₅ C(CH₃)₃ 1683 S Br OCH₂C₆H₅ C(CH₃)₃ 1684 S NO₂ OCH₂C₆H₅ C(CH₃)₃ 1685 S SCH₃ OCH₂C₆H₅ C(CH₃)₃ 1686 S SO₂CH₃ OCH₂C₆H₅ C(CH₃)₃ 1687 S SO₂CH₂CH₃ OCH₂C₆H₅ C(CH₃)₃ 1688 S CH₃ OCH₂C₆H₅ C(CH₃)₃ 1689 S CF₃ OCH₂C₆H₅ C(CH₃)₃ 1690 S OCHF₂ OCH₂C₆H₅ C(CH₃)₃ 1691 SO₂ F OCH₂C₆H₅ C(CH₃)₃ 1692 SO₂ Cl OCH₂C₆H₅ C(CH₃)₃ 1693 SO₂ Br OCH₂C₆H₅ C(CH₃)₃ 1694 SO₂ NO₂ OCH₂C₆H₅ C(CH₃)₃ 1695 SO₂ SCH₃ OCH₂C₆H₅ C(CH₃)₃ 1696 SO₂ SO₂CH₃ OCH₂C₆H₅ C(CH₃)₃ 1697 SO₂ SO₂CH₂CH₃ OCH₂C₆H₅ C(CH₃)₃ 1698 SO₂ CH₃ OCH₂C₆H₅ C(CH₃)₃ 1699 SO₂ CF₃ OCH₂C₆H₅ C(CH₃)₃ 1700 SO₂ OCHF₂ OCH₂C₆H₅ C(CH₃)₃ 1701 bond F OSO₂(4-CH₃—C₆H₄) CH(CH₃)₂ 1702 bond Cl OSO₂(4-CH₃—C₆H₄) CH(CH₃)₂ 1703 bond Br OSO₂(4-CH₃—C₆H₄) CH(CH₃)₂ 1704 bond NO₂ OSO₂(4-CH₃—C₆H₄) CH(CH₃)₂ 1705 bond SCH₃ OSO₂(4-CH₃—C₆H₄) CH(CH₃)₂ 1706 bond SO₂CH₃ OSO₂(4-CH₃—C₆H₄) CH(CH₃)₂ 1707 bond SO₂CH₂CH₃ OSO₂(4-CH₃—C₆H₄) CH(CH₃)₂ 1708 bond CH₃ OSO₂(4-CH₃—C₆H₄) CH(CH₃)₂ 1709 bond CF₃ OSO₂(4-CH₃—C₆H₄) CH(CH₃)₂ 1710 bond OCHF₂ OSO₂(4-CH₃—C₆H₄) CH(CH₃)₂ 1711 CH₂ F OSO₂(4-CH₃—C₆H₄) CH(CH₃)₂ 1712 CH₂ Cl OSO₂(4-CH₃—C₆H₄) CH(CH₃)₂ 1713 CH₂ Br OSO₂(4-CH₃—C₆H₄) CH(CH₃)₂ 1714 CH₂ NO₂ OSO₂(4-CH₃—C₆H₄) CH(CH₃)₂ 1715 CH₂ SCH₃ OSO₂(4-CH₃—C₆H₄) CH(CH₃)₂ 1716 CH₂ SO₂CH₃ OSO₂(4-CH₃—C₆H₄) CH(CH₃)₂ 1717 CH₂ SO₂CH₂CH₃ OSO₂(4-CH₃—C₆H₄) CH(CH₃)₂ 1718 CH₂ CH₃ OSO₂(4-CH₃—C₆H₄) CH(CH₃)₂ 1719 CH₂ CF₃ OSO₂(4-CH₃—C₆H₄) CH(CH₃)₂ 1720 CH₂ OCHF₂ OSO₂(4-CH₃—C₆H₄) CH(CH₃)₂ 1721 O F OSO₂(4-CH₃—C₆H₄) CH(CH₃)₂ 1722 O Cl OSO₂(4-CH₃—C₆H₄) CH(CH₃)₂ 1723 O Br OSO₂(4-CH₃—C₆H₄) CH(CH₃)₂ 1724 O NO₂ OSO₂(4-CH₃—C₆H₄) CH(CH₃)₂ 1725 O SCH₃ OSO₂(4-CH₃—C₆H₄) CH(CH₃)₂ 1726 O SO₂CH₃ OSO₂(4-CH₃—C₆H₄) CH(CH₃)₂ 1727 O SO₂CH₂CH₃ OSO₂(4-CH₃—C₆H₄) CH(CH₃)₂ 1728 O CH₃ OSO₂(4-CH₃—C₆H₄) CH(CH₃)₂ 1729 O CF₃ OSO₂(4-CH₃—C₆H₄) CH(CH₃)₂ 1730 O OCHF₂ OSO₂(4-CH₃—C₆H₄) CH(CH₃)₂ 1731 S F OSO₂(4-CH₃—C₆H₄) CH(CH₃)₂ 1732 S Cl OSO₂(4-CH₃—C₆H₄) CH(CH₃)₂ 1733 S Br OSO₂(4-CH₃—C₆H₄) CH(CH₃)₂ 1734 S NO₂ OSO₂(4-CH₃—C₆H₄) CH(CH₃)₂ 1735 S SCH₃ OSO₂(4-CH₃—C₆H₄) CH(CH₃)₂ 1736 S SO₂CH₃ OSO₂(4-CH₃—C₆H₄) CH(CH₃)₂ 1737 S SO₂CH₂CH₃ OSO₂(4-CH₃—C₆H₄) CH(CH₃)₂ 1738 S CH₃ OSO₂(4-CH₃—C₆H₄) CH(CH₃)₂ 1739 S CF₃ OSO₂(4-CH₃—C₆H₄) CH(CH₃)₂ 1740 S OCHF₂ OSO₂(4-CH₃—C₆H₄) CH(CH₃)₂ 1741 SO₂ F OSO₂(4-CH₃—C₆H₄) CH(CH₃)₂ 1742 SO₂ Cl OSO₂(4-CH₃—C₆H₄) CH(CH₃)₂ 1743 SO₂ Br OSO₂(4-CH₃—C₆H₄) CH(CH₃)₂ 1744 SO₂ NO₂ OSO₂(4-CH₃—C₆H₄) CH(CH₃)₂ 1745 SO₂ SCH₃ OSO₂(4-CH₃—C₆H₄) CH(CH₃)₂ 1746 SO₂ SO₂CH₃ OSO₂(4-CH₃—C₆H₄) CH(CH₃)₂ 1747 SO₂ SO₂CH₂CH₃ OSO₂(4-CH₃—C₆H₄) CH(CH₃)₂ 1748 SO₂ CH₃ OSO₂(4-CH₃—C₆H₄) CH(CH₃)₂ 1749 SO₂ CF₃ OSO₂(4-CH₃—C₆H₄) CH(CH₃)₂ 1750 SO₂ OCHF₂ OSO₂(4-CH₃—C₆H₄) CH(CH₃)₂ 1751 bond F OSO₂(4-CH₃—C₆H₄) C(CH₃)₃ 1752 bond Cl OSO₂(4-CH₃—C₆H₄) C(CH₃)₃ 1753 bond Br OSO₂(4-CH₃—C₆H₄) C(CH₃)₃ 1754 bond NO₂ OSO₂(4-CH₃—C₆H₄) C(CH₃)₃ 1755 bond SCH₃ OSO₂(4-CH₃—C₆H₄) C(CH₃)₃ 1756 bond SO₂CH₃ OSO₂(4-CH₃—C₆H₄) C(CH₃)₃ 1757 bond SO₂CH₂CH₃ OSO₂(4-CH₃—C₆H₄) C(CH₃)₃ 1758 bond CH₃ OSO₂(4-CH₃—C₆H₄) C(CH₃)₃ 1759 bond CF₃ OSO₂(4-CH₃—C₆H₄) C(CH₃)₃ 1760 bond OCHF₂ OSO₂(4-CH₃—C₆H₄) C(CH₃)₃ 1761 CH₂ F OSO₂(4-CH₃—C₆H₄) C(CH₃)₃ 1762 CH₂ Cl OSO₂(4-CH₃—C₆H₄) C(CH₃)₃ 1763 CH₂ Br OSO₂(4-CH₃—C₆H₄) C(CH₃)₃ 1764 CH₂ NO₂ OSO₂(4-CH₃—C₆H₄) C(CH₃)₃ 1765 CH₂ SCH₃ OSO₂(4-CH₃—C₆H₄) C(CH₃)₃ 1766 CH₂ SO₂CH₃ OSO₂(4-CH₃—C₆H₄) C(CH₃)₃ 1767 CH₂ SO₂CH₂CH₃ OSO₂(4-CH₃—C₆H₄) C(CH₃)₃ 1768 CH₂ CH₃ OSO₂(4-CH₃—C₆H₄) C(CH₃)₃ 1769 CH₂ CF₃ OSO₂(4-CH₃—C₆H₄) C(CH₃)₃ 1770 CH₂ OCHF₂ OSO₂(4-CH₃—C₆H₄) C(CH₃)₃ 1771 O F OSO₂(4-CH₃—C₆H₄) C(CH₃)₃ 1772 O Cl OSO₂(4-CH₃—C₆H₄) C(CH₃)₃ 1773 O Br OSO₂(4-CH₃—C₆H₄) C(CH₃)₃ 1774 O NO₂ OSO₂(4-CH₃—C₆H₄) C(CH₃)₃ 1775 O SCH₃ OSO₂(4-CH₃—C₆H₄) C(CH₃)₃ 1776 O SO₂CH₃ OSO₂(4-CH₃—C₆H₄) C(CH₃)₃ 1777 O SO₂CH₂CH₃ OSO₂(4-CH₃—C₆H₄) C(CH₃)₃ 1778 O CH₃ OSO₂(4-CH₃—C₆H₄) C(CH₃)₃ 1779 O CF₃ OSO₂(4-CH₃—C₆H₄) C(CH₃)₃ 1780 O OCHF₂ OSO₂(4-CH₃—C₆H₄) C(CH₃)₃ 1781 S F OSO₂(4-CH₃—C₆H₄) C(CH₃)₃ 1782 S Cl OSO₂(4-CH₃—C₆H₄) C(CH₃)₃ 1783 S Br OSO₂(4-CH₃—C₆H₄) C(CH₃)₃ 1784 S NO₂ OSO₂(4-CH₃—C₆H₄) C(CH₃)₃ 1785 S SCH₃ OSO₂(4-CH₃—C₆H₄) C(CH₃)₃ 1786 S SO₂CH₃ OSO₂(4-CH₃—C₆H₄) C(CH₃)₃ 1787 S SO₂CH₂CH₃ OSO₂(4-CH₃—C₆H₄) C(CH₃)₃ 1788 S CH₃ OSO₂(4-CH₃—C₆H₄) C(CH₃)₃ 1789 S CF₃ OSO₂(4-CH₃—C₆H₄) C(CH₃)₃ 1790 S OCHF₂ OSO₂(4-CH₃—C₆H₄) C(CH₃)₃ 1791 SO₂ F OSO₂(4-CH₃—C₆H₄) C(CH₃)₃ 1792 SO₂ Cl OSO₂(4-CH₃—C₆H₄) C(CH₃)₃ 1793 SO₂ Br OSO₂(4-CH₃—C₆H₄) C(CH₃)₃ 1794 SO₂ NO₂ OSO₂(4-CH₃—C₆H₄) C(CH₃)₃ 1795 SO₂ SCH₃ OSO₂(4-CH₃—C₆H₄) C(CH₃)₃ 1796 SO₂ SO₂CH₃ OSO₂(4-CH₃—C₆H₄) C(CH₃)₃ 1797 SO₂ SO₂CH₂CH₃ OSO₂(4-CH₃—C₆H₄) C(CH₃)₃ 1798 SO₂ CH₃ OSO₂(4-CH₃—C₆H₄) C(CH₃)₃ 1799 SO₂ CF₃ OSO₂(4-CH₃—C₆H₄) C(CH₃)₃ 1800 SO₂ OCHF₂ OSO₂(4-CH₃—C₆H₄) C(CH₃)₃ 1801 bond F SCH₃ CH(CH₃)₂ 1802 bond Cl SCH₃ CH(CH₃)₂ 1803 bond Br SCH₃ CH(CH₃)₂ 1804 bond NO₂ SCH₃ CH(CH₃)₂ 1805 bond SCH₃ SCH₃ CH(CH₃)₂ 1806 bond SO₂CH₃ SCH₃ CH(CH₃)₂ 1807 bond SO₂CH₂CH₃ SCH₃ CH(CH₃)₂ 1808 bond CH₃ SCH₃ CH(CH₃)₂ 1809 bond CF₃ SCH₃ CH(CH₃)₂ 1810 bond OCHF₂ SCH₃ CH(CH₃)₂ 1811 CH₂ F SCH₃ CH(CH₃)₂ 1812 CH₂ Cl SCH₃ CH(CH₃)₂ 1813 CH₂ Br SCH₃ CH(CH₃)₂ 1814 CH₂ NO₂ SCH₃ CH(CH₃)₂ 1815 CH₂ SCH₃ SCH₃ CH(CH₃)₂ 1816 CH₂ SO₂CH₃ SCH₃ CH(CH₃)₂ 1817 CH₂ SO₂CH₂CH₃ SCH₃ CH(CH₃)₂ 1818 CH₂ CH₃ SCH₃ CH(CH₃)₂ 1819 CH₂ CF₃ SCH₃ CH(CH₃)₂ 1820 CH₂ OCHF₂ SCH₃ CH(CH₃)₂ 1821 O F SCH₃ CH(CH₃)₂ 1822 O Cl SCH₃ CH(CH₃)₂ 1823 O Br SCH₃ CH(CH₃)₂ 1824 O NO₂ SCH₃ CH(CH₃)₂ 1825 O SCH₃ SCH₃ CH(CH₃)₂ 1826 O SO₂CH₃ SCH₃ CH(CH₃)₂ 1827 O SO₂CH₂CH₃ SCH₃ CH(CH₃)₂ 1828 O CH₃ SCH₃ CH(CH₃)₂ 1829 O CF₃ SCH₃ CH(CH₃)₂ 1830 O OCHF₂ SCH₃ CH(CH₃)₂ 1831 S F SCH₃ CH(CH₃)₂ 1832 S Cl SCH₃ CH(CH₃)₂ 1833 S Br SCH₃ CH(CH₃)₂ 1834 S NO₂ SCH₃ CH(CH₃)₂ 1835 S SCH₃ SCH₃ CH(CH₃)₂ 1836 S SO₂CH₃ SCH₃ CH(CH₃)₂ 1837 S SO₂CH₂CH₃ SCH₃ CH(CH₃)₂ 1838 S CH₃ SCH₃ CH(CH₃)₂ 1839 S CF₃ SCH₃ CH(CH₃)₂ 1840 S OCHF₂ SCH₃ CH(CH₃)₂ 1841 SO₂ F SCH₃ CH(CH₃)₂ 1842 SO₂ Cl SCH₃ CH(CH₃)₂ 1843 SO₂ Br SCH₃ CH(CH₃)₂ 1844 SO₂ NO₂ SCH₃ CH(CH₃)₂ 1845 SO₂ SCH₃ SCH₃ CH(CH₃)₂ 1846 SO₂ SO₂CH₃ SCH₃ CH(CH₃)₂ 1847 SO₂ SO₂CH₂CH₃ SCH₃ CH(CH₃)₂ 1848 SO₂ CH₃ SCH₃ CH(CH₃)₂ 1849 SO₂ CF₃ SCH₃ CH(CH₃)₂ 1850 SO₂ OCHF₂ SCH₃ CH(CH₃)₂ 1851 bond F SCH₃ C(CH₃)₃ 1852 bond Cl SCH₃ C(CH₃)₃ 1853 bond Br SCH₃ C(CH₃)₃ 1854 bond NO₂ SCH₃ C(CH₃)₃ 1855 bond SCH₃ SCH₃ C(CH₃)₃ 1856 bond SO₂CH₃ SCH₃ C(CH₃)₃ 1857 bond SO₂CH₂CH₃ SCH₃ C(CH₃)₃ 1858 bond CH₃ SCH₃ C(CH₃)₃ 1859 bond CF₃ SCH₃ C(CH₃)₃ 1860 bond OCHF₂ SCH₃ C(CH₃)₃ 1861 CH₂ F SCH₃ C(CH₃)₃ 1862 CH₂ Cl SCH₃ C(CH₃)₃ 1863 CH₂ Br SCH₃ C(CH₃)₃ 1864 CH₂ NO₂ SCH₃ C(CH₃)₃ 1865 CH₂ SCH₃ SCH₃ C(CH₃)₃ 1866 CH₂ SO₂CH₃ SCH₃ C(CH₃)₃ 1867 CH₂ SO₂CH₂CH₃ SCH₃ C(CH₃)₃ 1868 CH₂ CH₃ SCH₃ C(CH₃)₃ 1869 CH₂ CF₃ SCH₃ C(CH₃)₃ 1870 CH₂ OCHF₂ SCH₃ C(CH₃)₃ 1871 O F SCH₃ C(CH₃)₃ 1872 O Cl SCH₃ C(CH₃)₃ 1873 O Br SCH₃ C(CH₃)₃ 1874 O NO₂ SCH₃ C(CH₃)₃ 1875 O SCH₃ SCH₃ C(CH₃)₃ 1876 O SO₂CH₃ SCH₃ C(CH₃)₃ 1877 O SO₂CH₂CH₃ SCH₃ C(CH₃)₃ 1878 O CH₃ SCH₃ C(CH₃)₃ 1879 O CF₃ SCH₃ C(CH₃)₃ 1880 O OCHF₂ SCH₃ C(CH₃)₃ 1881 S F SCH₃ C(CH₃)₃ 1882 S Cl SCH₃ C(CH₃)₃ 1883 S Br SCH₃ C(CH₃)₃ 1884 S NO₂ SCH₃ C(CH₃)₃ 1885 S SCH₃ SCH₃ C(CH₃)₃ 1886 S SO₂CH₃ SCH₃ C(CH₃)₃ 1887 S SO₂CH₂CH₃ SCH₃ C(CH₃)₃ 1888 S CH₃ SCH₃ C(CH₃)₃ 1889 S CF₃ SCH₃ C(CH₃)₃ 1890 S OCHF₂ SCH₃ C(CH₃)₃ 1891 SO₂ F SCH₃ C(CH₃)₃ 1892 SO₂ Cl SCH₃ C(CH₃)₃ 1893 SO₂ Br SCH₃ C(CH₃)₃ 1894 SO₂ NO₂ SCH₃ C(CH₃)₃ 1895 SO₂ SCH₃ SCH₃ C(CH₃)₃ 1896 SO₂ SO₂CH₃ SCH₃ C(CH₃)₃ 1897 SO₂ SO₂CH₂CH₃ SCH₃ C(CH₃)₃ 1898 SO₂ CH₃ SCH₃ C(CH₃)₃ 1899 SO₂ CF₃ SCH₃ C(CH₃)₃ 1900 SO₂ OCHF₂ SCH₃ C(CH₃)₃ 1901 bond F Cl CH(CH₃)₂ 1902 bond Cl Cl CH(CH₃)₂ 1903 bond Br Cl CH(CH₃)₂ 1904 bond NO₂ Cl CH(CH₃)₂ 1905 bond SCH₃ Cl CH(CH₃)₂ 1906 bond SO₂CH₃ Cl CH(CH₃)₂ 1907 bond SO₂CH₂CH₃ Cl CH(CH₃)₂ 1908 bond CH₃ Cl CH(CH₃)₂ 1909 bond CF₃ Cl CH(CH₃)₂ 1910 bond OCHF₂ Cl CH(CH₃)₂ 1911 CH₂ F Cl CH(CH₃)₂ 1912 CH₂ Cl Cl CH(CH₃)₂ 1913 CH₂ Br Cl CH(CH₃)₂ 1914 CH₂ NO₂ Cl CH(CH₃)₂ 1915 CH₂ SCH₃ Cl CH(CH₃)₂ 1916 CH₂ SO₂CH₃ Cl CH(CH₃)₂ 1917 CH₂ SO₂CH₂CH₃ Cl CH(CH₃)₂ 1918 CH₂ CH₃ Cl CH(CH₃)₂ 1919 CH₂ CF₃ Cl CH(CH₃)₂ 1920 CH₂ OCHF₂ Cl CH(CH₃)₂ 1921 O F Cl CH(CH₃)₂ 1922 O Cl Cl CH(CH₃)₂ 1923 O Br Cl CH(CH₃)₂ 1924 O NO₂ Cl CH(CH₃)₂ 1925 O SCH₃ Cl CH(CH₃)₂ 1926 O SO₂CH₃ Cl CH(CH₃)₂ 1927 O SO₂CH₂CH₃ Cl CH(CH₃)₂ 1928 O CH₃ Cl CH(CH₃)₂ 1929 O CF₃ Cl CH(CH₃)₂ 1930 O OCHF₂ Cl CH(CH₃)₂ 1931 S F Cl CH(CH₃)₂ 1932 S Cl Cl CH(CH₃)₂ 1933 S Br Cl CH(CH₃)₂ 1934 S NO₂ Cl CH(CH₃)₂ 1935 S SCH₃ Cl CH(CH₃)₂ 1936 S SO₂CH₃ Cl CH(CH₃)₂ 1937 S SO₂CH₂CH₃ Cl CH(CH₃)₂ 1938 S CH₃ Cl CH(CH₃)₂ 1939 S CF₃ Cl CH(CH₃)₂ 1940 S OCHF₂ Cl CH(CH₃)₂ 1941 SO₂ F Cl CH(CH₃)₂ 1942 SO₂ Cl Cl CH(CH₃)₂ 1943 SO₂ Br Cl CH(CH₃)₂ 1944 SO₂ NO₂ Cl CH(CH₃)₂ 1945 SO₂ SCH₃ Cl CH(CH₃)₂ 1946 SO₂ SO₂CH₃ Cl CH(CH₃)₂ 1947 SO₂ SO₂CH₂CH₃ Cl CH(CH₃)₂ 1948 SO₂ CH₃ Cl CH(CH₃)₂ 1949 SO₂ CF₃ Cl CH(CH₃)₂ 1950 SO₂ OCHF₂ Cl CH(CH₃)₂ 1951 bond F Cl C(CH₃)₃ 1952 bond Cl Cl C(CH₃)₃ 1953 bond Br Cl C(CH₃)₃ 1954 bond NO₂ Cl C(CH₃)₃ 1955 bond SCH₃ Cl C(CH₃)₃ 1956 bond SO₂CH₃ Cl C(CH₃)₃ 1957 bond SO₂CH₂CH₃ Cl C(CH₃)₃ 1958 bond CH₃ Cl C(CH₃)₃ 1959 bond CF₃ Cl C(CH₃)₃ 1960 bond OCHF₂ Cl C(CH₃)₃ 1961 CH₂ F Cl C(CH₃)₃ 1962 CH₂ Cl Cl C(CH₃)₃ 1963 CH₂ Br Cl C(CH₃)₃ 1964 CH₂ NO₂ Cl C(CH₃)₃ 1965 CH₂ SCH₃ Cl C(CH₃)₃ 1966 CH₂ SO₂CH₃ Cl C(CH₃)₃ 1967 CH₂ SO₂CH₂CH₃ Cl C(CH₃)₃ 1968 CH₂ CH₃ Cl C(CH₃)₃ 1969 CH₂ CF₃ Cl C(CH₃)₃ 1970 CH₂ OCHF₂ Cl C(CH₃)₃ 1971 O F Cl C(CH₃)₃ 1972 O Cl Cl C(CH₃)₃ 1973 O Br Cl C(CH₃)₃ 1974 O NO₂ Cl C(CH₃)₃ 1975 O SCH₃ Cl C(CH₃)₃ 1976 O SO₂CH₃ Cl C(CH₃)₃ 1977 O SO₂CH₂CH₃ Cl C(CH₃)₃ 1978 O CH₃ Cl C(CH₃)₃ 1979 O CF₃ Cl C(CH₃)₃ 1980 O OCHF₂ Cl C(CH₃)₃ 1981 S F Cl C(CH₃)₃ 1982 S Cl Cl C(CH₃)₃ 1983 S Br Cl C(CH₃)₃ 1984 S NO₂ Cl C(CH₃)₃ 1985 S SCH₃ Cl C(CH₃)₃ 1986 S SO₂CH₃ Cl C(CH₃)₃ 1987 S SO₂CH₂CH₃ Cl C(CH₃)₃ 1988 S CH₃ Cl C(CH₃)₃ 1989 S CF₃ Cl C(CH₃)₃ 1990 S OCHF₂ Cl C(CH₃)₃ 1991 SO₂ F Cl C(CH₃)₃ 1992 SO₂ Cl Cl C(CH₃)₃ 1993 SO₂ Br Cl C(CH₃)₃ 1994 SO₂ NO₂ Cl C(CH₃)₃ 1995 SO₂ SCH₃ Cl C(CH₃)₃ 1996 SO₂ SO₂CH₃ Cl C(CH₃)₃ 1997 SO₂ SO₂CH₂CH₃ Cl C(CH₃)₃ 1998 SO₂ CH₃ Cl C(CH₃)₃ 1999 SO₂ CF₃ Cl C(CH₃)₃ 2000 SO₂ OCHF₂ Cl C(CH₃)₃

Very particular preference is also given to the compounds of the formula Ia2 (≡Ia where R¹, R², R⁵ and R¹²=H, R³=CH₃, l=1), in particular to the compounds Ia2.n, where the variables X, R⁴, R¹⁰ and R¹¹ are as defined in Table 1.

Very particular preference is also given to the compounds of the formula Ia3 (≡Ia where R¹, R², R⁵ and R¹²=H, R³═CH₃, l=1), in particular to the compounds Ia3.n, where the variables X, R⁴, R¹⁰ and R¹¹ are as defined in Table 1.

Very particular preference is also given to the compounds of the formula Ia4 (≡Ia where R¹, R², R⁵ and R¹²=H, R³=CH₃, l=2), in particular to the compounds Ia4.n, where the variables X, R⁴, R¹⁰ and R¹¹ are as defined in Table 1.

Very particular preference is also given to the compounds of the formula Ia5 (≡Ia where R¹, R², R⁵ and R¹²=H, R³=CH₃, l=1), in particular to the compounds Ia5.n, where the variables X, R⁴, R¹⁰ and R¹¹ are as defined in Table 1.

Very particular preference is also given to the compounds of the formula Ia6 (≡Ia where R¹, R², R⁵ and R¹²=H, R³=CH₃, l=2), in particular to the compounds Ia6.n, where the variables X, R⁴, R¹⁰ and R¹¹ are as defined in Table 1.

Very particular preference is also given to the compounds of the formula Ia7 (≡Ia where R¹, R², R⁵ and R¹²=H, l=0), in particular to the compounds Ia7.n, where the variables X, R⁴, R¹⁰ and R¹¹ are as defined in Table 1.

Very particular preference is also given to the compounds of the formula Ia8 (≡Ia where R¹, R², R⁵ and R¹²=H, R³=CH³, l=1), in particular to the compounds Ia8.n, where the variables X, R⁴, R¹⁰ and R¹¹ are as defined in Table 1.

Very particular preference is also given to the compounds of the formula Ia9 (≡Ia where R¹, R², R⁵ and R¹²=H, l=0), in particular to the compounds Ia9.n, where the variables X, R⁴, R¹⁰ and R¹¹ are as defined in Table 1.

Very particular preference is also given to the compounds of the formula Ia10 (≡Ia where R¹, R², R⁵ and R¹²=H, l=0), in particular to the compounds Ia10.n, where the variables X, R⁴, R¹⁰ and R¹¹ are as defined in Table 1.

Very particular preference is also given to the compounds of the formula Ia11 (≡Ia where R¹, R², R⁵ and R¹²=H, l=0), in particular to the compounds Ia11.n, where the variables X, R⁴, R¹⁰ and R¹¹ are as defined in Table 1.

Very particular preference is also given to the compounds of the formula Ia12 (≡Ia where R¹, R², R⁵ and R¹²=H, l=0), in particular to the compounds Ia12.n, where the variables X, R⁴, R¹⁰ and R¹¹ are as defined in Table 1.

Very particular preference is also given to the compounds of the formula Ia13 (=Ia where R¹, R², R⁵ and R¹²=H, l=0), in particular to the compounds Ia13.n, where the variables X, R⁴, R¹⁰ and R¹¹ are as defined in Table 1.

Very particular preference is also given to the compounds of the formula Ia14 (≡Ia where R¹, R², R⁵ and R¹²=H, R³=CH₃, l=1), in particular to the compounds Ia14.n, where the variables X, R⁴, R¹⁰ and R¹¹ are as defined in Table 1.

Very particular preference is also given to the compounds of the formula Ia15 (≡Ia where R¹, R², R⁵ and R¹²=H, R³=CH₃, l=1), in particular to the compounds Ia15.n, where the variables X, R⁴, R¹⁰ and R¹¹ are as defined in Table 1.

Very particular preference is also given to the compounds of the formula Ia16 (≡Ia where R¹, R², R⁵ and R¹²=H, l=0), in particular to the compounds Ia16.n, where the variables X, R⁴, R¹⁰ and R¹¹ are as defined in Table 1.

Very particular preference is also given to the compounds of the formula Ia17 (≡Ia where R¹, R², R⁵ and R¹²=H, l=0), in particular to the compounds Ia17.n, where the variables X, R⁴, R¹⁰ and R¹¹ are as defined in Table 1.

Very particular preference is also given to the compounds of the formula Ia18 (≡Ia where R¹, R², R⁵ and R¹²=H, R¹³=CH₃, l=1), in particular to the compounds Ia18.n, where the variables X, R⁴, R¹⁰ and R¹¹ are as defined in Table 1.

Very particular preference is also given to the compounds of the formula Ia19 (≡Ia where R¹, R², R⁵ and R¹²=H, l=0), in particular to the compounds Ia19.n, where the variables X, R⁴, R¹⁰ and R¹¹ are as defined in Table 1.

Very particular preference is also given to the compounds of the formula Ia20 (≡Ia where R¹, R², R⁵ and R¹²=H, l=0), in particular to the compounds Ia20.n, where the variables X, R⁴, R¹⁰ and R¹¹ are as defined in Table 1.

Very particular preference is also given to the compounds of the formula Ia21 (≡Ia where R¹, R², R⁵ and R¹²=H, l=0), in particular to the compounds Ia21.n, where the variables X, R⁴, R¹⁰ and R¹¹ are as defined in Table 1.

Very particular preference is also given to the compounds of the formula Ia22 (≡Ia where R¹, R², R⁵ and R¹²=H, R³=CH₃, l=1), in particular to the compounds Ia22.n, where the variables X, R⁴, R¹⁰ and R¹¹ are as defined in Table 1.

The tricyclic benzoylpyrazole derivatives of the formula I can be obtained by various routes, for example by one of the following processes:

-   A. Preparation of compounds of the formula I where R¹⁰=halogen by     reacting a tricyclic benzoylpyrazole derivative of the formula Iα     (≡I where R¹⁰=hydroxyl) with a halogenating agent:     -   Suitable halogenating agents are, for example, phosgene,         diphosgene, triphosgene, thionyl chloride, oxalyl chloride,         phosphorus oxychloride, phosphorus pentachloride, mesyl         chloride, chloromethylene-N,N-dimethylammonium chloride, oxalyl         bromide, phosphorus oxybromide, etc.     -   The starting materials are generally employed in equimolar         amounts. However, it may also be advantageous to employ an         excess of one or the other component.     -   Suitable solvents are, for example, chlorinated hydrocarbons,         such as methylene chloride or 1,2-dichloroethane, aromatic         hydrocarbons, for example toluene, xylene or chlorobenzene,         polar aprotic solvents, such as acetonitrile, dimethylformamide         or dimethyl sulfoxide, or mixtures of these. However, it is also         possible to carry out the reaction in the absence of solvent.     -   The reaction temperature is generally in the range from 0° C. to         the boiling point of the reaction mixture.     -   Work-up can be carried out in a manner known per se to afford         the product. -   B. Preparation of compounds of the formula I where R¹⁰=OR¹³, by     reacting a tricyclic benzoylpyrazole derivative of the formula Iα     (≡I where R¹⁰=hydroxyl) with an alkylating agent III.     -   L¹ is a nucleophilically replaceable leaving group, such as         halogen, for example chlorine or bromine, hetaryl, for example         imidazolyl, carboxylate, for example acetate, or sulfonate, for         example mesylate or triflate, etc.     -   The compounds of the formula III can be employed directly, such         as, for example, in the case of the carbonyl halides, or be         generated in situ, for example activated carboxylic acids (using         carboxylic acid and dicyclohexylcarbodiimide etc.).     -   The starting materials are generally employed in equimolar         amounts. However, it may also be advantageous to employ an         excess of one or the other component.     -   If appropriate, it may also be advantageous to carry out the         reaction in the presence of a base. Here, the reactants and the         base are advantageously employed in equimolar amounts. In         certain cases, an excess of base, for example from 1.5 to 3         molar equivalents, may be advantageous.     -   Suitable bases are tertiary alkylamines, such as triethylamine,         aromatic amines, such as pyridine, alkali metal carbonates, for         example sodium carbonate or potassium carbonate, alkali metal         bicarbonates, for example sodium bicarbonate and potassium         bicarbonate, alkali metal alkoxides, such as sodium methoxide,         sodium ethoxide, potassium tert-butoxide, or alkali metal         hydrides, for example sodium hydride. Preference is given to         using triethylamine or pyridine.     -   Suitable solvents are, for example, chlorinated hydrocarbons,         such as methylene chloride or 1,2-dichloroethane, aromatic         hydrocarbons, for example toluene, xylene or chlorobenzene,         ethers, such as diethyl ether, methyl tert-butyl ether,         tetrahydrofuran or dioxane, polar aprotic solvents, such as         acetonitrile, dimethylformamide or dimethyl sulfoxide, or         esters, such as ethyl acetate, or mixtures of these.     -   The reaction temperature is generally in the range from 0° C. to         the boiling point of the reaction mixture.     -   Work-up can be carried out in a manner known per se to afford         the product. -   C. Preparation of compounds of the formula I where R¹⁰=OR¹³, SR¹³,     NR¹⁵R¹⁶ or N-bonded heterocyclyl by reacting compounds of the     formula Iβ (≡I where R¹⁰=halogen) with a compound of the formula     IVα, IVβ, IVγ or IVδ, if appropriate in the presence of a base or     with prior formation of salt.     -   The starting materials are generally employed in equimolar         amounts. However, it may also be advantageous to employ an         excess of one or the other component.     -   If appropriate, it may also be advantageous to carry out the         reaction in the presence of a base. Here, the reactants and the         base are advantageously employed in equimolar amounts. An excess         of base, for example from 1.5 to 3 molar equivalents, based on         Iβ (where R¹⁰=halogen), may be advantageous in certain cases.     -   Suitable bases are tertiary alkylamines, such as triethylamine,         aromatic amines, such as pyridine, alkali metal carbonates, for         example sodium carbonate or potassium carbonate, alkali metal         bicarbonates, for example sodium bicarbonate and potassium         bicarbonate, alkali metal alkoxides, such as sodium methoxide,         sodium ethoxide, potassium tert-butoxide, or alkali metal         hydrides, for example sodium hydride. Preference is given to         using sodium hydride or potassium tert-butoxide.     -   Suitable solvents are, for example, chlorinated hydrocarbons,         such as methylene chloride or 1,2-dichloroethane, aromatic         hydrocarbons, for example toluene, xylene or chlorobenzene,         ethers, such as diethyl ether, methyl tert-butyl ether,         tetrahydrofuran or dioxane, polar aprotic solvents, such as         acetonitrile, dimethylformamide or dimethyl sulfoxide, or         mixtures of these.     -   The reaction temperature is generally in the range from 0° C. to         the boiling point of the reaction mixture.     -   Work-up can be carried out in a manner known per se to afford         the product. -   D. Preparation of compounds of the formula I where R¹⁰=SO₂R¹⁴ by     reacting compounds of the formula I where R¹⁰=SR¹⁰ (Iγ) with an     oxidizing agent.     -   Suitable oxidizing agents are, for example, m-chloroperbenzoic         acid, peroxyacetic acid, trifluoroperoxyacetic acid, hydrogen         peroxide, if appropriate in the presence of a catalyst, such as         tungstate.     -   The starting materials are generally employed in equimolar         amounts. However, it may also be advantageous to employ an         excess of one or the other component.     -   Suitable solvents are, for example, chlorinated hydrocarbons,         such as methylene chloride or 1,2-dichloroethane, aromatic         hydrocarbons, for example, toluene, xylene or chlorobenzene,         ethers, such as diethyl ether, methyltert-butyl ether,         tetrahydrofuran or dioxane, polar aprotic solvents, such as         acetonitrile or dimethylformamide, or esters, such as ethyl         acetate, or mixtures of these.     -   The reaction temperature is generally in the range from 0° C. to         the boiling point of the reaction mixture.     -   Work-up can be carried out in a manner known per se to afford         the product. -   E. Preparation of compounds of the formula I where R⁹=IIa (where     R¹⁰+ hydroxyl or mercapto) by reacting a metalated pyrazole     derivative of the formula V with a tricyclic benzoic acid derivative     of the formula VIα:     -   Here, M is a metal, in particular an alkali metal, such as         lithium or sodium, an alkaline earth metal, such as, for         example, magnesium, or a transition metal, such as palladium,         nickel, etc. and L² is a nucleophilically replaceable leaving         group, such as halogen, for example chlorine or bromine,         alkylsulfonate, such as mesylate, haloalkylsulfonate, such as         triflate, or cyanide.     -   The reaction is generally carried out at temperatures of from         −100° C. to the reflux temperature of the reaction mixture.         Suitable solvents are inert aprotic solvents, such as ethers,         for example diethyl ether, tetrahydrofuran. The compounds of the         formula VIα are generally employed in excess, but it may also be         advantageous to employ them in equimolar amounts or in         substoichiometric amounts. Work-up is carried out to afford the         product.     -   The metalated pyrazole derivatives of the formula V can be         formed in a manner known per se by reacting pyrazoles which are         halogenated in the 4-position with metals, such as lithium,         sodium, magnesium, etc., or with organometallic compounds, such         as, for example, butyllithium. However, it is also possible to         metalate pyrazoles which are linked in the 4 position to         hydrogen directly, for example with the abovementioned metals or         organometallic compounds. The reactions are generally carried         out in an inert aprotic solvent, preferably in ether, such as         diethyl ether, tetrahydrofuran, etc. The reaction temperature is         in the range from −100° C. to the boiling point of the reaction         mixture. The compounds of the formula V are generally directly         reacted further or generated in situ. -   F. Preparation of compounds of the formula Iα (≡I where     R¹⁰=hydroxyl) by reacting an activated tricyclic benzoic acid of the     formula VIβ or a tricyclic benzoic acid VIγ, preferably activated in     situ, with a pyrazole of the formula VII to give the acylation     product, followed by rearrangement.

L³ is a nucleophilically replaceable leaving group, such as halogen, for example bromine or chlorine, hetaryl, for example imidazolyl or pyridyl, carboxylate, for example acetate or trifluoroacetate, etc.

The activated tricyclic benzoic acid VIβ can be employed directly, such as in the case of the tricyclic benzoyl halides, or be generated in situ, for example using dicyclohexylcarbodiimide, triphenylphosphine/azodicarboxylic ester, 2-pyridine disulfide/triphenylphosphine, carbonyldiimidazole, etc.

If appropriate, it may be advantageous to carry out the acylation reaction in the presence of a base. Here, the reactants and the auxiliary base are advantageously employed in equimolar amounts. A slight excess of auxiliary base, for example from 1.2 to 1.5 molar equivalents, based on VI, may be advantageous in certain cases.

Suitable auxiliary bases are tertiary alkylamines, pyridine, or alkali metal carbonates. Suitable solvents are, for example, chlorinated hydrocarbons, such as methylene chloride or 1,2-dichloroethane, aromatic hydrocarbons, such as toluene, xylene or chlorobenzene, ethers, such as diethyl ether, methyl tert-butyl ether, tetrahydrofuran or dioxane, polar aprotic solvents, such as acetonitrile, dimethylformamide or dimethyl sulfoxide, or esters, such as ethyl acetate, or mixtures of these.

If tricyclic benzoyl halides are employed as activated carboxylic acid components, it may be advantageous to cool the reaction mixture to 0-10° C. when adding this reaction partner. The mixture is subsequently stirred at 20-100° C., preferably at 25-50° C., until the reaction has gone to completion. Work-up is carried out in a customary manner, for example by pouring the reaction mixture into water and extracting the product of value. Solvents which are suitable for this purpose are, in particular, methylene chloride, diethyl ether and ethyl acetate. The organic phase is dried and the solvent removed, and the crude ester can then be employed for the rearrangement without further purification.

The rearrangement of the esters VIII to give the compounds of the formula Iα is advantageously carried out at from 20 to 100° C. in a solvent and in the presence of a base and, if appropriate, using a cyano compound as catalyst.

Solvents which may be used are, for example, acetonitrile, methylene chloride, 1,2-dichloroethane, dioxane, ethyl acetate, toluene or mixtures of these. Preferred solvents are acetonitrile and dioxane.

Suitable bases are tertiary amines, such as triethylamine, aromatic amines, such as pyridine, or alkali metal carbonates, such as sodium carbonate or potassium carbonate, which are preferably employed in equimolar amounts or in an up to four-fold excess, based on the ester. Preference is given to using triethylamine or alkali metal carbonate, preferably in double the equimolar ratio, based on the ester.

Suitable cyano compounds are inorganic cyanides, such as sodium cyanide or potassium cyanide, and organic cyano compounds, such as acetone cyanohydrin or trimethylsilyl cyanide. They are employed in an amount of from 1 to 50 mol percent, based on the ester. Preference is given to using acetone cyanohydrin or trimethylsilyl cyanide, for example in an amount of from 5 to 15, preferably 10, mol percent, based on the ester.

Work-up may be carried out in a manner known per se. The reaction mixture is, for example, acidified using dilute mineral acid, such as 5% strength hydrochloric acid or sulfuric acid, and extracted with an organic solvent, for example methylene chloride or ethyl acetate. The organic extract can be extracted with 5-10% strength alkali metal carbonate solution, for example sodium carbonate or potassium carbonate solution. The aqueous phase is acidified and the resulting precipitate is filtered off with suction and/or extracted with methylene chloride or ethyl acetate, the extract being dried and concentrated.

However, it is also possible to generate the ester VIII in situ by reacting a pyrazole of the formula VII, or an alkali metal salt thereof, with a tricyclic benzene derivative of the formula IX in the presence of carbon monoxide, a catalyst and a base.

L⁴ is a leaving group, such as halogen, for example chlorine, bromine or iodine, or sulfonate such as mesylate or triflate; preference is given to bromine or triflate.

If appropriate, the ester VIII reacts directly to give the tricyclic benzoylpyrazole derivative of the formula Iα.

Suitable catalysts are palladium ligand complexes in which the palladium is present in oxidation state 0, metallic palladium, if appropriate applied to a support, and preferably palladium(II) salts. The reaction with palladium(II) salts and metallic palladium is preferably carried out in the presence of complex ligands.

A suitable palladium(0) ligand complex is, for example, tetrakis(triphenylphosphane)palladium.

Metallic palladium is preferably applied to an inert carrier, such as, for example, activated carbon, silica, alumina, barium sulfate or calcium carbonate. The reaction is preferably carried out in the presence of complex ligands, such as, for example, triphenylphosphane.

Suitable palladium(II) salts are, for example, palladium acetate and palladium chloride. Preference is given to carrying out the reaction in the presence of complex ligands such as, for example, triphenylphosphane.

Suitable complex ligands for the palladium ligand complexes, or complex ligands in whose presence the reaction with metallic palladium or palladium(II) salts is preferably carried out are tertiary phosphanes whose structure is represented by the following formulae:

where n is a number from 1 to 4 and the radicals R^(a) to R^(g) are C₁-C₆-alkyl, aryl-C₁-C₂-alkyl or preferably aryl. Aryl is, for example, naphthyl and unsubstituted or substituted phenyl such as, for example, 2-tolyl and in particular unsubstituted phenyl.

The complex palladium salts can be prepared in a manner known per se starting from commercially available palladium salts, such as palladium chloride or palladium acetate, and the corresponding phosphanes, such as, for example, triphenylphosphane or 1,2-bis(diphenylphosphano)ethane. A large number of complexed palladium salts is also commercially available. Preferred palladium salts are [(R)-(+)-2,2′-bis(diphenylphosphano)-1,1′-binaphthyl]palladium(II) chloride, bis(triphenylphosphane)palladium(II) acetate and in particular bis(triphenylphosphane)palladium(II) chloride.

The palladium catalyst is generally employed in a concentration of from 0.05 to 5 mol %, and preferably of 1-3 mol %.

Suitable bases are tertiary amines, such as, for example, N-methylpiperidine, ethyldiisopropylamine, 1,8-bisdimethylaminonaphthalene and in particular triethylamine. Also suitable are alkali metal carbonates, such as sodium carbonate or potassium carbonate. However, mixtures of potassium carbonate and triethylamine are also suitable.

In general, from 2 to 4 molar equivalents, in particular 2 molar equivalents, of the alkali metal carbonate, and from 1 to 4 molar equivalents, in particular 2 molar equivalents, of the tertiary amine are employed, based on the tricyclic benzene derivative of the formula IX.

Suitable solvents are nitrites, such as benzonitrile and acetonitrile, amides, such as dimethylformamide, dimethylacetamide, tetra-C₁-C₄-alkylureas or N-methylpyrrolidone, and preferably ethers, such as tetrahydrofuran, methyl tert-butyl ether. Particular preference is given to using, as solvents, ethers such as 1,4-dioxane and dimethoxyethane.

The tricyclic benzoyl halides of the formula VIβ where L³=Cl, Br can be prepared in a manner known per se by reacting the tricyclic benzoic acids of the formula VIγ (≡VIb) with halogenating agents such as thionyl chloride, thionyl bromide, phosgene, diphosgene, triphosgene, oxalyl chloride and oxalyl bromide.

In a known manner, the tricyclic benzoic acids of the formula VIγ (≡VIb) can be prepared by acidic or basic hydrolysis from the corresponding esters VIc.

Tricyclic benzoic acid derivatives of the formula VI

where:

-   -   X is oxygen, sulfur, S═O, S(═O)₂, CR⁶R⁷, NR⁸ or a bond;     -   Y together with the two carbons to which it is attached forms a         saturated, partially saturated or unsaturated 5- or 6-membered         heterocycle which contains one to three identical or different         heteroatoms selected from the following group: oxygen, sulfur or         nitrogen;     -   R¹, R², R⁶, R⁷ are hydrogen, C₁-C₆-alkyl, C₁-C₆-haloalkyl,         C₁-C₆-alkoxy or C₁-C₆-haloalkoxy;     -   R³ is halogen, C₁-C₆-alkyl, C₁-C₆-haloalkyl, C₁-C₆-alkoxy or         C₁-C₆-haloalkoxy;     -   R⁴ is nitro, halogen, cyano, C₁-C₆-alkyl, C₁-C₆-haloalkyl,         C₁-C₆-alkoxy, C₁-C₆-haloalkoxy, C₁-C₆-alkylthio,         C₁-C₆-haloalkylthio, C₁-C₆-alkylsulfinyl,         C₁-C₆-haloalkylsulfinyl, C₁-C₆-alkylsulfonyl,         C₁-C₆-haloalkylsulfonyl, aminosulfonyl,         N—(C₁-C₆-alkyl)-aminosulfonyl, N,N-di(C₁-C₆-alkyl)aminosulfonyl,         N—(C₁-C₆-alkylsulfonyl) amino, N—(C₁-C₆-haloalkylsulfonyl)amino,         N—(C₁-C₆-alkyl)-N—(C₁-C₆-alkylsulfonyl)amino or         N—(C₁-C₆-alkyl)-N—(C₁-C₆-haloalkylsulfonyl)amino;     -   R⁵ is hydrogen, C₁-C₆-alkyl or halogen;     -   R⁸ is hydrogen, C₁-C₆-alkyl, C₁-C₆-haloalkyl,         C₁-C₆-alkylcarbonyl, formyl, C₁-C₆-alkoxycarbonyl,         C₁-C₆-haloalkoxycarbonyl, C₁-C₆-alkylsulfonyl or         C₁-C₆-haloalkylsulfonyl;     -   l is 0, 1 or 2;     -   R¹⁷ is hydroxyl or a radical which can be removed by hydrolysis;         are novel.

Examples of radicals which can be removed by hydrolysis are alkoxy, phenoxy, alkylthio and phenylthio radicals which can be unsubstituted or substituted, halides, heteroaryl radicals which are attached via nitrogen, amino and imino radicals which may be unsubstituted or substituted, etc.

Preference is given to tricyclic benzoyl halides VIa (VI where R¹⁷=halogen)

where the variables X, Y, R¹ to R⁵ and l are as defined under formula VI and

-   -   Hal is halogen, in particular chloride or bromide.

Preference is also given to tricyclic benzoic acids of the formula VIb (VI where R¹⁷=hydroxyl; ≡VIγ),

where the variables X, Y, R¹ to R⁵ and l are as defined under formula VI.

Preference is also given to tricyclic benzoic esters of the formula VIc (VI where R¹⁷=T=C₁-C₆-alkoxy),

where the variables X, Y, R¹ to R⁵ and l are as defined under formula VI and

-   -   T is C₁-C₆-alkoxy.

With respect to the variables X, Y, R¹ to R⁵ and l, the particularly preferred embodiments of the tricyclic benzoic acid derivatives of the formulae VI, VIa, VIb and VIc correspond to those of the tricyclic benzoylpyrazole derivatives of the formula I.

Particular preference is given to the compounds VI, VIa, VIb and VIc where Y together with the two carbons to which it is attached forms the following heterocycles:

Here, extraordinary preference is given to the compounds VI, VIa, VIb and VIc where

-   -   R⁴ is nitro, halogen, C₁-C₆-alkyl, C₁-C₆-haloalkyl,         C₁-C₆-alkoxy, C₁-C₆-alkylthio or C₁-C₆-alkylsulfonyl; in         particular C₁-C₆-alkylsulfonyl.

The tricyclic benzoic esters VIc can be obtained in different ways.

For example, benzoic esters of the formula X, which are prepared in a manner known per se (cf., for example, Chem. Pharm. Bull. 1985, 33 (8), 3336; Helv. Chim. Acta 1987, 70, 1326; J. Chem. Soc. Perkin Trans. 1972, 2019; J. Chem. Soc. Perkin Trans. 1991, 2763; Tetrahydron Asymmetry 1998, 9, 1137), can be cyclized to cyclic ketones of the formula XI (cf., for example, Chem. Ber. 1923, 56, 1819; J. Chem. Soc. Perkin 11991, 2763; J. Med. Chem. 1988, 31, 230; Tetrahedron 1987, 43, 4549; Synlett 1991, 6, 443; Chem. Pharm. Bull. 1985, 33 (8), 3336). Analogously to known processes (cf., for example, J. Heterocyclic Chem. 1976, 13, 545; J. Heterocyclic Chem. 1972, 9, 1341; J. Org. Chem. 1978, 43, 3015; J. Chem. Soc. Perkin Trans. I 1978, 86; J. Org. Chem. 1986, 51, 2021), these can be converted into the tricyclic benzoic esters of the formula VIc.

Furthermore, it may be suitable to cyclize the cyclic ketone of the formula XI in a manner known per se (XII), for example using an anhydride or acid anhydride, if appropriate in the presence of catalytic amounts of a Lewis acid, such as boron trifluoride (cf., for example, Can. J. Chem. 1979, 57, 3292; J. Am. Chem. Soc. 1953, 75, 626), followed by reaction with a hydrazine (cf. A. R. Katritzky et al., Comprehensive Heterocyclic Chemistry, Vol. 5, p. 121, 277-280 (1984), Pergamon Press; J. Org. Chem. 1961, 26, 451; Org. Synth. 1949, 29, 54), where the resulting pyrazole radical can be modified further by customary processes.

Furthermore, the diketone XII can be reacted with hydroxylamine or equivalents thereof (cf. A. R. Katritzky et al., Comprehensive Heterocyclic Chemistry, Vol. 6, p. 61-64, 118 (1984), Pergamon Press; Chem. Ber. 1967, 100, 3326). This gives the corresponding isoxazole derivatives which can be modified further by customary processes.

It is also possible to react the diketone XII with amidines (cf., for example, A. R. Katritzky et al., Comprehensive Heterocyclic Chemistry, Vol. 3, p. 112-114 (1924), Pergamon Press; J. Chem. Soc. C 1967, 1922; Org. Synth. 1963, IV, 182). If required, the resulting pyrimidine derivatives can be modified further by customary processes.

In the reactA123ions mentioned above, it is also possible to employ, instead of the diketone XII, equivalents thereof, such as enol ethers or enamines, which can be prepared analogously to known processes.

It may also be possible to react the cyclic ketone of the formula XI analogously to known processes with an aldehyde or ketone to give (XIII) (cf., for example, Tetrahedron Lett. 1978, 2111; Tetrahedron Lett. 1981, 5251; Chem. Ber. 1960, 2294; J. Chem. Soc. Perkin Trans. 1, 1991, 1467; Tetrahedron Lett. 1992, 8091). The resulting unsaturated cyclic ketone of the formula XIII can be reacted with a hydrazine in a manner known per se (cf., for example, A. R. Katritzky et al. Comprehensive Heterocyclic Chemistry, Vol. 2, 6 (1984), Pergamon Press; J. Heterocyclic Chem. 1969, 533; J. Heterocyclic Chem. 1968, 853), where the resulting pyrazoline can be modified further by customary processes.

It is furthermore possible to react the unsaturated cyclic ketone of the formula XIII with hydroxylamine or equivalents thereof (Z. Chem. 1980, 20, 19). This gives the corresponding isoxazoline derivatives, which can be modified further by customary processes.

Furthermore, it is possible to convert aldehydes of the formula XIV, which can be prepared in a manner known per se, analogously to processes known from the literature by reaction with a hydrazine or hydroxylamine (or equivalents of these) into the corresponding hydrazones or oximes (cf., for example, Synth. Commun. 1990, 20, 1373; J. Org. Chem. 1980, 45, 3756). These in turn can be converted in a manner known per se into the corresponding 1,3-dipoles, which then react in a [3+2]-cycloaddition to give the compounds VIc (cf., for example, Synth. Commun. 1990, 20, 1373; EP-A 386 892; J. Org. Chem. 1980, 45, 3756; Tetrahedron Lett. 1981, 22, 1333.)

The resulting pyrazoles or pyrazolines and isoxazoles or isoxazolines can be modified further by customary processes.

It is also possible to react the cyclic ketone of the formula XI with a dithiol or a “mixed alcohol” analogously to processes known from the literature (cf., for example, T. W. Greene et al., Protective Groups in Organic Synthesis, John Wiley & Sons, 133-140), and to subject it subsequently to a rearrangement in the presence of bromine or a suitable Lewis acid, such as, for example, tellurium tetrachloride (cf. Tetrahedron 1991, 47, 4187; Synthesis 1991, 223; J. Chem. Soc. Chem. Commun. 1985, 1645).

The resulting heterocycles can, if desired, be modified further by processes known per se.

The abovementioned substitutents R^(3a) are hydrogen, C₁-C₆-alkyl, C₁-C₆-haloalkyl, hydroxyl, C₁-C₆-alkoxy or C₁-C₆-haloalkoxy; furthermore, the abovementioned radicals R^(3b) are hydrogen, C₁-C₆-alkyl or C₁-C₆-haloalkyl.

The tricyclic benzoic esters of the formula VIc or the tricyclic benzoic acids of the formula VIb can be obtained by reacting a tricyclic benzene derivative of the formula IX with a C₁-C₆-alcohol or water in the presence of carbon monoxide, a catalyst and a base. In general, the conditions mentioned under process F apply.

L⁴ is a leaving group, such as halogen, for example chlorine, bromine or iodine, or sulfate, such as mesylate or triflate; preference is given to bromine or triflate.

Furthermore, the tricyclic benzoic acids of the formula VIb can be obtained by converting a tricyclic benzene derivative of the formula IX where L⁴ is halogen, such as chlorine or bromine, in particular bromine, by reaction with, for example, n-butyllithium or magnesium into the metalated derivative, followed by quenching with carbon dioxide (cf., for example, J. Org. Chem. 1990, 55, 773; Angew. Chem. Int. Ed. 1969, 8, 68).

It is also possible to obtain the tricyclic benzoic acids VIb by hydrolyzing the corresponding nitrites, analogously to processes known from the literature. The nitriles for their part can be obtained by halogen/nitrile exchange or by Sandmeyer reaction from the corresponding anilines XV.

The compounds of the formula IX,

where:

-   -   X is oxygen, sulfur, S═O, S(═O)₂, CR⁶R⁷, NR⁸ or a bond;     -   Y together with the two carbons to which it is attached forms a         saturated, partially saturated or unsaturated 5- or 6-membered         heterocycle which contains one to three identical or different         heteroatoms selected from the following group: oxygen, sulfur or         nitrogen;     -   R¹, R², R⁶, R⁷ are hydrogen, C₁-C₆-alkyl, C₁-C₆-haloalkyl,         C₁-C₆-alkoxy or C₁-C₆-haloalkoxy;     -   R³ is halogen, C₁-C₆-alkyl, C₁-C₆-haloalkyl, C₁-C₆-alkoxy or         C₁-C₆-haloalkoxy;     -   R⁴ is nitro, halogen, cyano, C₁-C₆-alkyl, C₁-C₆-haloalkyl,         C₁-C₆-alkoxy, C₁-C₆-haloalkoxy, C₁-C₆-alkylthio,         C₁-C₆-haloalkylthio, C₁-C₆-alkylsulfinyl,         C₁-C₆-haloalkylsulfinyl, C₁-C₆-alkylsulfonyl,         C₁-C₆-haloalkylsulfonyl, aminosulfonyl,         N—(C₁-C₆-alkyl)aminosulfonyl, N,N-di(C₁-C₆-alkyl)aminosulfonyl,         N—(C₁-C₆-alkylsulfonyl)amino, N—(C₁-C₆-haloalkylsulfonyl)amino,         N—(C₁-C₆-alkyl)-N—(C₁-C₆-alkylsulfonyl)amino or         N—(C₁-C₆-alkyl)-N—(C₁-C₆-haloalkylsulfonyl) amino;     -   R⁵ is hydrogen, C₁-C₆-alkyl or halogen;     -   R⁸ is hydrogen, C₁-C₆-alkyl, C₁-C₆-haloalkyl,         C₁-C₆-alkylcarbonyl, formyl, C₁-C₆-alkoxycarbonyl,         C₁-C₆-haloalkoxycarbonyl, C₁-C₆-alkylsulfonyl or         C₁-C₆-haloalkylsulfonyl;     -   l is 0, 1 or 2;     -   L⁴ is halogen, C₁-C₆-alkylsulfonyloxy,         C₁-C₆-haloalkylsulfonyloxy or phenylsulfonyloxy, where the         phenyl ring of the lastmentioned radical may be unsubstituted or         partially or fully halogenated and/or may carry one to three of         the following radicals: nitro, cyano, C₁-C₆-alkyl,         C₁-C₆-haloalkyl, C₁-C₄-alkoxy or C₁-C₄-haloalkoxy;         are novel.

Preference is given to compounds of the formula IX where L⁴ is halogen, in particular bromine.

The particularly preferred embodiments of the compounds of the formula IX with respect to the variables X, Y, R¹ to R⁵ and l correspond to those of the tricyclic benzoylpyrazole derivatives of the formula I.

Particular preference is given to the compounds of the formula IX where

-   -   Y together with the two carbons to which it is attached forms         the following heterocycles:

Here, extraordinary preference is given to the compounds IX where

-   -   R⁴ is nitro, halogen, C₁-C₆-alkyl, C₁-C₆-haloalkyl,         C₁-C₆-alkoxy, C₁-C₆-alkylthio or C₁-C₆-alkylsulfonyl; in         particular C₁-C₆-alkylsulfonyl.

The compounds of the formula IX can be obtained in different ways, the fused system, for example, can be constructed analogously to the processes described for the compounds of the formula VIc.

However, it is also possible to construct the fused system from a suitable parent compound (analogously to the processes described for compounds of the formula VIc) and to introduce L⁴=halogen subsequently by customary halogenating reactions.

The anilines of the formula XV and the nitriles of the formula XVI

where:

-   -   X is oxygen, sulfur, S═O, S(═O)₂, CR⁶R⁷, NR⁸ or a bond;     -   Y together with the two carbons to which it is attached forms a         saturated, partially saturated or unsaturated 5- or 6-membered         heterocycle which contains one to three identical or different         heteroatoms selected from the following group: oxygen, sulfur or         nitrogen;     -   R¹, R², R⁶, R⁷ are hydrogen, C₁-C₆-alkyl, C₁-C₆-haloalkyl,         C₁-C₆-alkoxy or C₁-C₆-haloalkoxy;     -   R³ is halogen, C₁-C₆-alkyl, C₁-C₆-haloalkyl, C₁-C₆-alkoxy or         C₁-C₆-haloalkoxy;     -   R⁴ is nitro, halogen, cyano, C₁-C₆-alkyl, C₁-C₆-haloalkyl,         C₁-C₆-alkoxy, C₁-C₆-haloalkoxy, C₁-C₆-alkylthio,         C₁-C₆-haloalkylthio, C₁-C₆-alkylsulfinyl,         C₁-C₆-haloalkylsulfinyl, C₁-C₆-alkylsulfonyl,         C₁-C₆-haloalkylsulfonyl, aminosulfonyl,         N—(C₁-C₆-alkyl)aminosulfonyl, N,N-di(C₁-C₆-alkyl)aminosulfonyl,         N—(C₁-C₆-alkylsulfonyl) amino, N—(C₁-C₆-haloalkylsulfonyl)amino,         N—(C₁-C₆-alkyl)-N—(C₁-C₆-alkylsulfonyl)amino or         N—(C₁-C₆-alkyl)-N—(C₁-C₆-haloalkylsulfonyl)amino;     -   R⁵ is hydrogen, C₁-C₆-alkyl or halogen;     -   R⁸ is hydrogen, C₁-C₆-alkyl, C₁-C₆-haloalkyl,         C₁-C₆-alkylcarbonyl, formyl, C₁-C₆-alkoxycarbonyl,         C₁-C₆-haloalkoxycarbonyl, C₁-C₆-alkylsulfonyl or         C₁-C₆-haloalkylsulfonyl;     -   l is 0, 1 or 2;         are also novel.

The particularly preferred embodiments of the compounds of the formulae XV and XVI with respect to the variables X, Y, R¹ to R⁵ and l correspond to those of the tricyclic benzoylpyrazole derivatives of the formula I.

Particular preference is given to the compounds of the formula XV or XVI where

-   -   Y together with the two carbons to which it is attached forms         the following heterocycles:

Here, extraordinary preference is given to the compounds XV or XVI where

-   -   R⁴ is nitro, halogen, C₁-C₆-alkyl, C₁-C₆-haloalkyl,         C₁-C₆-alkoxy, C₁-C₆-alkylthio or C₁-C₆-alkylsulfonyl; in         particular C₁-C₆-alkylsulfonyl.

The compounds of the formula XV can be obtained in different ways; for example, the fused system can be constructed analogously to the processes described for the compounds of the formula VIc.

However, it is also possible to construct the fused system from a suitable parent compound (analogously to the processes described for the compounds of the formula VIc) and to introduce a nitro group subsequently by nitration para to R⁴, analogously to processes known from the literature, and to convert this group in a manner known per se by reduction into the amino group.

If appropriate, it may be advantageous in the synthesis variants described above to introduce protective groups for certain functionalities if the functionalities are not compatible with the reaction conditions required.

The selection of the protective groups depends both on the reaction conditions and on the structure of the molecule. The protective groups, their introduction and their removal are generally known from the literature (cf., for example, T. W. Greene et al., “Protective Groups in Organic Synthesis”, 2^(nd) edition, Wiley, New York, 1991), and they can be employed analogously to processes known from the literature.

Furthermore, it may be necessary to carry out a combination of the synthesis variants described above.

It is also possible to introduce further substitutents or to modify the substitutents present by electrophilic, nucleophilic, free-radical or organometallic reactions and by oxidation or reduction reactions.

PREPARATION EXAMPLES 1. (5-Phenylcarbonyloxy-1-methyl-1H-pyrazol-4-yl)-(8-methyl-sulfonyl-3a,4-dihydro-3H-indeno[1,2-c]isoxazol-5-yl)methanone (compound 2.2) 2-Allyl-6-chlorobenzaldehyde

Under an atmosphere of protective gas, a solution of 10.89 g (0.107 mol) of trimethylethylenediamine in 50 ml of anhydrous tetrahydrofuran was cooled to −10° C. and admixed dropwise with 66.6 ml of a 1.6 molar solution of n-butyllithium in hexane (0.107 mol). After 10 minutes, 15 g (0.107 mol) of 6-chlorobenzaldehyde in 70 ml of tetrahydrofuran were added dropwise, and the mixture was admixed with a further 0.214 mol of n-butyllithium in hexane (146.8 ml) and stirred at 0° C. for 2.5 hours. The mixture was cooled to −20° C., 12.42 g (0.139 mol) of copper(I) cyanide were added, the mixture was stirred at −10° C. for 30 minutes, and 28.42 g of allyl bromide in 100 ml of tetrahydrofuran were then added dropwise. The mixture was stirred at 0° C. for another 2.5 hours, and 230 ml of saturated ammonium chloride solution were then added dropwise. The resulting solid was separated off and the aqueous phase was extracted with diethyl ether. The combined organic phases were then washed with saturated ammonium chloride solution and dried, and the solvent was removed under reduced pressure. This gave 17.0 g of 2-allyl-6-chlorobenzaldehyde (89%) in the form of a dark oil.

¹H NMR (CDCl₃, δ in ppm): 3.73 (d, 2H); 5.05 (dd, 2H); 5.96 (m, 1H); 7.05-7.48 (m, 3H); 10.58 (s, 1H).

2-Allyl-6-chlorobenzaldehyde oxime

5.58 g of sodium bicarbonate were added to a solution of 4.62 g of hydroxylamine hydrochloride in 50 ml of water, and the mixture was cooled to 0° C. A solution of 9.7 g (44.32 mmol) of 2-allyl-6-chlorobenzaldehyde in 50 ml of methanol was then added dropwise, and the mixture was stirred at room temperature overnight. The methanol was subsequently removed under reduced pressure and the residue was stirred into 300 ml of water. The aqueous phase was extracted with diethyl ether and the combined organic phases were washed with saturated ammonium chloride solution and dried, and the solvent was removed. This gave 8.7 g (quantitative) of 2-allyl-6-chlorobenzaldehyde oxime in the form of a viscous oil.

¹H NMR (CDCl₃, δ in ppm): 3.58 (d, 2H); 5.02 (2d, 2H); 5.95 (m, 1H); 7.08-7.36 (m, 3H); 8.49 (s, 1H).

8-Chloro-3a,4-dihydro-3H-indeno[1,2-c]isoxazole

At room temperature, 37.0 ml of a sodium hypochlorite solution (12.5% of active chlorine) were added dropwise to a solution of 8.4 g (42.9 mmol) of 2-allyl-6-chlorobenzaldehyde oxime in 100 ml of methylene chloride, and a spatula tip of sodium acetate was added. The mixture was stirred at room temperature for 2 hours, the organic phase was separated off, the aqueous phase was extracted with methylene chloride and the combined organic phases were washed with saturated ammonium chloride solution. The organic phase was dried and the solvent was removed. This gave 7.0 g (94%) of 8-chloro-3a,4-dihydro-3H-indeno-[1,2-c]isoxazole in the form of a viscous oil.

¹H NMR (CDCl₃, δ in ppm): 2.81 (dd, 1H); 3.24 (dd, 1H); 3.78-4.03 (s, 2H); 4.78 (t, 1H); 7.23-7.41 (m, 3H).

8-Methylthio-3a,4-dihydro-3H-indeno[1,2c]isoxazole

At room temperature, 3.6 g (52.0 mmol) of sodium thiomethoxide were added to a solution of 5.0 g (25.8 mmol) of 8-chloro-3a,4-dihydro-3H-indeno-[1,2-c]isoxazole in 60 ml of N-methylpyrrolidone, and the mixture was stirred overnight. The mixture was subsequently stirred into 800 ml of water, the aqueous phase was extracted with diethyl ether, the combined organic phases were washed with saturated ammonium chloride solution and dried, and the solvent was removed. This gave 4.6 g (87%) of 8-methylthio-3a,4-dihydro-3H-indeno[1,2-c]isoxazole in the form of a dark brown solid.

¹H NMR (CDCl₃, δ in ppm): 2.54 (s, 3H); 2.78 (dd, 1H); 3.21 (dd, 1H); 3.72-3.93 (s, 2H); 4.64 (t, 1H); 7.09-7.38 (m, 3H).

5-Bromo-8-methylthio-3a,4-dihydro-3H-indeno[1,2-c]isoxazole

120 ml of sulfuric acid (98 percent strength) were cooled to 0° C., and 11.2 g (54.8 mmol) of 8-methylthio-3a,4-dihydro-3H-indeno[1,2-c]isoxazole were added a little at a time. 9.2 g (57.5 mmol) of bromine were then added dropwise, and stirring was continued at 0° C. for another 2 hours. The resulting solution was poured into 2 l of a mixture of water and ice, this mixture was stirred for 1.5 hours and the precipitated solid was filtered off with suction and then washed and dried. This gave 11.4 g (73%) of 5-bromo-8-methylthio-3a,4-dihydro-3H-indeno[1,2-c]isoxazole of a brown solid having a m.p. of 127-135° C.

¹H NMR (CDCl₃, δ in ppm): 2.53 (s, 3H); 2.71 (dd, 1H); 3.24 (dd, 1H); 3.81-4.02 (s, 2H); 4.71 (t, 1H); 7.01 (d, 1H); 7.47 (d, 1H).

5-Bromo-8-methylsulfonyl-3a,4-dihydro-3H-indeno[1,2-c]-isoxazole

A solution of 11.2 g (39.4 mmol) of 5-bromo-8-methylthio-3a,4-dihydro-3H-indeno[1,2-c]isoxazole and 1.55 g of sodium tungstate in 250 ml of toluene and 50 ml of glacial acetic acid was heated to 70° C. and mixed dropwise with 10.73 g (39 percent strength, 86.8 mmol) of hydrogen peroxide. Stirring was continued at 70° C. for another 3 hours, and a solid precipitated out. The mixture was allowed to cool to room temperature and stirred into 1 l of water, and the white solid was filtered off with suction. The organic phase of the filtrate was separated off and the aqueous phase was extracted with ethyl acetate. The combined organic phases were washed with water and dried, and the solvent was removed. This gave a viscous brown oil which was stirred with hexane/ethyl acetate (4:1). The resulting precipitate was filtered off with suction and combined with the solid obtained above. This gave 7.3 g (59%) of 5-bromo-8-methylsulfonyl-3a,4-dihydro-3H-indeno[1,2-c]-isoxazole.

¹H-NMR (d⁶-DMSO, δ in ppm): 2.93 (dd, 1H); 3.23 (dd, 1H); 3.41 (s, 3H); 3.94 (dd, 1H); 4.16 (m, 1H); 4.81 (t, 1H); 7.82 (d, 1H); 8.03 (d, 1H).

(5-Hydroxy-1-methyl-1H-pyrazol-4-yl)-(8-methylsulfonyl-3a,4-dihydro-3H-indeno[1,2-c]isoxazol-5-yl)methanone (compound 2.1)

0.62 g (6.33 mmol) of 5-hydroxy-1-methylpyrazole, 1.75 g (12.66 mmol) of dry potassium carbonate, 1.28 g (12.67 mmol) of triethylamine and 0.22 g (0.30 mmol) of bis-(triphenylphosphane)palladium dichloride were added to a suspension of 2.0 g (6.33 mmol) of 5-bromo-8-methylsulfonyl-3a,4-dihydro-3H-indeno[1,2-c]-isoxazole in 100 ml of dioxane. In a miniautoclave, a carbon monoxide pressure of 20 bar was applied, the mixture was stirred for 5 minutes and the autoclave was vented. This procedure was repeated 3 times. The autoclave was subsequently heated to 130° C., a carbon monoxide pressure of 20 bar was applied once more and the mixture was stirred for 24 hours. After cooling and venting, the solvent was removed, and the residue was taken up in water, adjusted to pH 11 and washed with methylene chloride. The mixture was subsequently acidified to pH 4 using 10 percent strength hydrochloric acid and extracted with methylene chloride. The combined organic phases were washed with saturated ammonium chloride solution and dried, and the solvent was removed. This gave 0.58 g (25%) of (5-hydroxy-1-methyl-1H-pyrazol-4-yl)-(8-methylsulfonyl-3a,4-dihydro-3H-indeno[1,2-c]isoxazole)-methanone in the form of a dark oil.

¹H NMR (CDCl₃, δ in ppm): 3.03 (dd, 1H); 3.42 (s, 3H); 3.40 (m, 1H); 3.51 (s, 3H); 4.05 (m, 2H); 4.85 (t, 1H); 7.57 (s, 1H); 7.92 (d, 1H); 8.22 (d, 1H).

(5-Phenylcarbonyloxy-1-methyl-1H-pyrazol-4-yl)-(8-methylsulfonyl-3a,4-dihydro-3H-indeno[1,2-c]isoxazol-5-yl)methanone (compound 2.2)

Under an atmosphere of protective gas, 0.18 g of triethylamine and 0.26 g (1.82 mmol) of benzoyl chloride in 10 ml of tetrahydrofuran were added at 0° C. to a suspension of 0.55 g (1.52 mmol) of (5-hydroxy-1-methyl-1H-pyrazol-4-yl)-(8-methylsulfonyl-3a,4-dihydro-3H-indeno[1,2-c]-isoxazol-5-yl)methanone in 10 ml of tetrahydrofuran. The mixture was stirred overnight at room temperature, the solvent was removed, the residue was taken up in ethyl acetate, washed with water and dried, and the solvent was removed. The crude product was purified by silica gel chromatography (mobile phase: ethyl acetate:hexane=1:1). This gave 0.22 g (31%) of (5-phenylcarbonyloxy-1-methyl-1H-pyrazol-4-yl)-(8-methylsulfonyl-3a,4-dihydro-3H-indeno[1,2-c]isoxazol-5-yl)methanone in the form of a yellow solid having a m.p. of 86-93° C.

¹H NMR (CDCl₃, δ in ppm): 3.22 (s, 3H); 3.34 (m, 2H); 3.81 (s, 3H); 3.98 (m, 2H); 4.81 (t, 1H); 7.20-8.21 (m, 8H).

2. 4-(2-Methyl-9-chloro-[1]-thiochromano[4,3-c]pyrazol-6-yl)carbonyl-5-hydroxy-1-methyl-1H-pyrazole (compound 3.1) Methyl 2-chlorosulfonyl-4-chlorobenzoate

At from 0 to 5° C., a solution of 60.9 g (0.88 mol) of sodium nitrite in 100 ml of water was added dropwise to a solution of 139 g (0.75 mol) of methyl 2-amino-4-chlorobenzoate in 400 ml of concentrated hydrochloric acid and the mixture was stirred at 0° C. for another hour.

In a second apparatus, 3 g of copper(II) chloride, 3 g of benzyltriethylammonium chloride, 10 ml of water and 400 ml of 1,2-dichloroethane were combined and 64 g (1 mol) of sulfur dioxide were introduced.

The diazonium salt described above was subsequently added at from 10 to 15° C., and the mixture was slowly heated to 50° C. A further 54 g (0.84 mol) of sulfur dioxide were then introduced, and stirring was continued at 50° C. for another 30 minutes. After cooling, 7.4 g (0.1 mol) of chlorine gas were then introduced at room temperature, stirring was continued for 15 minutes and the phases which had formed were then separated. The organic phase was dried and the solvent was removed. This gave 207 g of methyl 2-chlorosulfonyl-4-chlorobenzoate.

¹H NMR (CDCl₃, δ in ppm): 4.00 (s, 3H); 7.75 (m, 2H); 8.18 (m, 1H)

Methyl 2-mercapto-4-chlorobenzoate

Over a period of 1.5 hours, 243.5 g (3.7 mol) of zinc powder were added a little at a time to a suspension of 205 g (0.75 mol) of methyl 2-chlorosulfonyl-4-chlorobenzoate in 1 l of concentrated hydrochloric acid and 375 g of ice. The mixture was stirred for another 3 hours and slowly heated to 70° C. After 2 hours at this temperature, the mixture was cooled. The reaction mixture was allowed to stand at room temperature for 12 hours and then extracted with ethyl acetate, the combined organic phases were dried and the solvent was removed. This gave 125.4 g (83%) of methyl 2-mercapto-4-chlorobenzoate.

¹H NMR (CDCl₃, δ in ppm): 3.95 (s, 3H); 4.88 (s, 1H); 7.10 (m, 1H); 7.30 (m, 1H); 7.96 (d, 1H).

Methyl 2-(2-hydroxycarbonyleth-1-yl)thio-4-chlorobenzoate

179.5 g (1.3 mol) of potassium carbonate and, a little at a time, 94.5 g (0.62 mol) of 3-bromopropionic acid were added to a solution of 125.4 g (0.62 mol) of methyl 2-mercapto-4-chlorobenzoate in 1.5 l of acetone, and the reaction mixture was stirred at room temperature for 12 hours. The solvent was distilled off, the residue was taken up in water and the mixture was extracted with diethyl ether. The aqueous phase was then made acidic using concentrated hydrochloric acid, and the resulting precipitate was filtered off with suction and dried. This gave 150 g (88%) of methyl 2-(2-hydroxycarbonyleth-1-yl)thio-4-chlorobenzoate.

M.p.: 133 to 136° C.

Methyl 5-chloro-4-oxothiochromane-8-carboxylate

At 70° C., 50 g (0.18 mol) of methyl 2-(2-hydroxycarbonyleth-1-yl)thio-4-chlorobenzoate were added to 500 g of polyphosphoric acid, and the mixture was stirred for a further 30 minutes. The reaction mixture was then stirred into water and the resulting precipitate was filtered off with suction and dried. This gave 41.1 g (88%) of methyl 5-chloro-4-oxothiochromane-8-carboxylate.

¹H NMR (CDCl₃, δ in ppm): 3.08 (m, 4H); 3.96 (s, 3H); 7.14 (d, 1H); 7.95 (d, 1H).

Methyl 5-chloro-3-(N,N-dimethylaminomethylidene)-4-oxothiochromane-8-carboxylate

30 g (0.078 mol) of methyl 5-chloro-4-oxothiochromane-8-carboxylate in 300 ml of N,N-dimethylformamide dimethyl acetal were refluxed for 6 hours. Volatile components were then distilled off, the residue was taken up in methylene chloride and the organic phase washed with water. Drying and removal of the solvent gave 35.3 g (97%) of methyl 5-chloro-3-(N,N-dimethylaminomethylidene)-4-oxothiochromane-8-carboxylate.

¹H NMR (CDCl₃, δ in ppm): 3.18 (s, 6H); 3.80 (s, 2H); 3.95 (s, 3H); 7.24 (d, 1H); 7.64 (s, 1H); 7.82 (d, 1H).

2-Methyl-6-methoxycarbonyl-9-chloro-[1]-thiochromano[4,3-c]-pyrazole

1.3 g (29.2 mmol) of methylhydrazine were added dropwise to a solution of 7.0 g (22.5 mmol) of methyl 5-chloro-3-(N,N-dimethylaminomethylidene)-4-oxothiochromane-8-carboxylate in 700 ml of ethanol, and the mixture was refluxed for 2 hours. The solvent was removed and the residue was chromatographed over silica gel using ethyl acetate/cyclohexane (2:3) as mobile phase. This gave 4.0 g (60%) of 2-methyl-6-methoxycarbonyl-9-chloro-[1]-thiochromano[4,3-c]pyrazole.

¹H NMR (CDCl₃, δ in ppm): 3.76 (s, 2H); 3.95 (s, 3H); 4.00 (s, 3H); 7.24 (s, 1H); 7.36 (d, 1H); 7.70 (d, 1H).

2-Methyl-6-hydroxycarbonyl-9-chloro-[1]-thiochromano[4,3-c]pyrazole

4.0 g (13.6 mmol) of 2-methyl-6-methoxycarbonyl-9-chloro-[1]-thiochromano[4,3-c]pyrazole in 100 ml of methanol/water (1:1) were refluxed with 0.8 g (20 mmol) of sodium hydroxide for 1 hour. The organic solvent was removed under reduced pressure and the residue was extracted with ethyl acetate. The aqueous phase was acidified using concentrated hydrochloric acid and the resulting precipitate was filtered off with suction and dried. This gave 3.5 g (92%) of 2-methyl-6-hydroxycarbonyl-9-chloro-[1]-thiochromano[4,3-c]-pyrazole

¹H NMR (CDCl₃, δ in ppm): 3.80 (s, 2H); 3.96 (s, 3H); 7.40 (d, 1H); 7.65 (m, 2H).

4-(2-Methyl-9-chloro-[1]-thiochromano[4,3-c]pyrazol-6-yl)-carbonyl-5-hydroxy-1-methyl-1H-pyrazole (compound 3.1)

A mixture of 0.60 g (2.1 mmol) of 2-methyl-6-hydroxycarbonyl-9-chloro-[1]-thiochromano[4,3-c]-pyrazole and 0.21 g (2.1 mmol) of N,N-dicyclohexylcarbodiimide in 20 ml of acetonitrile was stirred at room temperature overnight. The mixture was admixed with in each case 500 ml of ethyl acetate and 2% strength sodium carbonate solution, the resulting precipitate was filtered off, the organic phase was dried and the solvent was removed. The residue was then refluxed with 0.59 g (4.3 mmol) of potassium carbonate in 5 ml of 1,4-dioxane for 3 hours. After cooling, the mixture was extracted with diethyl ether and the aqueous phase was acidified to pH 3. The resulting precipitate was filtered off with suction and dried. This gave 0.14 g of 4-(2-methyl-9-chloro-[1]-thiochromano[4,3-c]pyrazol-6-yl)-carbonyl-5-hydroxy-1-methyl-1H-pyrazole.

M.p.: 168-171° C.

3. (5-Hydroxy-1-methyl-1H-pyrazol-4-yl)-(6-methoxy-3a,4-dihydro-3H-chromeno[4,3-c]isoxazolin-9-yl)methanone (compound 2.3) Methyl 2-hydroxy-3-formyl-4-methoxybenzoate

At from 0 to 5° C., a solution of 209.0 g (1.1 mol) of titanium tetrachloride in 150 ml of methylene chloride was added dropwise to a solution of 50.1 g (0.275 mol) of methyl 2-hydroxy-4-methoxybenzoate and 88 g (0.725 mol) of dichloromethoxymethane in 400 ml of methylene chloride, and the mixture was stirred at room temperature overnight. The mixture was then stirred into ice-water and extracted with methylene chloride. The combined organic phases were washed with sodium bicarbonate solution, water and sodium chloride solution and dried, and the solvent was then removed. Silica gel chromatography using cyclohexane/ethyl acetate=1:1 gave 24.5 g (42%) of methyl 2-hydroxy-3-formyl-4-methoxybenzoate in the form of a colorless solid of m.p.: 123-124° C.

¹H NMR (CDCl₃, δ in ppm): 3.92 (s, 3H); 3.98 (s, 3H); 6.49 (d, 1H); 8.19 (d, 1H); 10.39 (s, 1H).

Methyl 2-allyloxy-3-formyl-4-methoxybenzoate

At room temperature, 23.2 g (0.192 mol) of allyl bromide were added dropwise to a mixture of 21.0 g (0.375 mol) of potassium hydroxide and 20.2 g (0.096 mol) of methyl 2-hydroxy-3-formyl-4-methoxybenzoate in 500 ml of dimethyl sulfoxide, and the mixture was stirred at room temperature for 4 hours. The mixture was subsequently stirred into 1.5 l of 3% strength aqueous hydrochloric acid and extracted with ethyl acetate. The combined organic phases were washed with water and dried, and the solvent was removed. Silica gel chromatography using cyclohexane/ethyl acetate=1:2 gave 7.7 g (36%) of methyl 2-allyloxy-3-formyl-4-methoxybenzoate in the form of a yellowish oil.

¹H NMR (CDCl₃, δ in ppm): 3.86 (s, 3H); 3.93 (s, 3H); 4.58 (d, 2H); 5.32 (d, 1H); 5.39 (d, 1H); 6.15 (m, 1H); 6.79 (d, 1H); 8.04 (d, 1H); 10.41 (s, 1H).

6-Methoxy-9-methoxycarbonyl-3a,4-dihydro-3H-chromeno[4,3-c]isoxazoline

Step a)

At room temperature, 4.6 g (18.4 mmol) of methyl 2-allyloxy-3-formyl-4-methoxybenzoate in 70 ml of methanol were added dropwise to a solution of 2.25 g (32.3 mmol) of hydroxylammonium chloride and 2.7 g of pyridine in 70 ml of water. The mixture was stirred at room temperature overnight, 150 ml of water were added, the mixture was extracted with methylene chloride, the combined organic phases were washed with 3% strength aqueous hydrochloric acid and dried, and the solvent was removed. The resulting oxime has a melting point of 126-129° C.

Step b)

This oxime was reacted further without any further purification by dissolving it in 40 ml of methylene chloride, followed by dropwise addition of 15.0 ml (25.0 mmol) of sodium hypochlorite solution (12.5% of active chlorine). A spatula tip of sodium acetate was added and the mixture was stirred at room temperature for 12 hours. The organic phase was separated off, the aqueous phase was extracted with methylene chloride, the combined organic phases were washed with water and dried, and the solvent was removed. Silica gel chromatography using cyclohexane/ethyl acetate=1:1 gave 2.2 g (49%) of 6-methoxy-9-methoxycarbonyl-3a,4-dihydro-3H-chromeno[4,3-c]-isoxazoline in the form of a colorless solid of m.p: 199-203° C.

¹H NMR (CDCl₃, δ in ppm): 3.84 (s, 3H); 3.98 (s, 3H); 3.8-4.0 (m, 2H); 4.16 (dt, 1H); 4.63 (t, 1H); 4.84 (dd, 1H); 6.61 (d, 1H); 7.93 (d, 1H).

6-Methoxy-9-hydroxycarbonyl-3a,4-dihydro-3H-chromeno[4,3-c]isoxazoline

At room temperature, a solution of 0.8 g (20.0 mmol) of sodium hydroxide in 7 ml of water was added dropwise to a solution of 2.1 g (8.0 mmol) of 6-methoxy-9-methoxycarbonyl-3a,4-dihydro-3H-chromeno[4,3-c]isoxazoline in 40 ml of methanol, and the mixture was refluxed for 6 hours. After cooling, the solvent was removed and the residue was taken up in about 50 ml of water and washed with methylene chloride. The aqueous phase was subsequently acidified using 10% strength hydrochloric acid (pH=1-2), and the precipitate was filtered off with suction, washed with water and dried at 60° C. This gave 1.7 g (86%) of 6-methoxy-9-hydroxycarbonyl-3a,4-dihydro-3H-chromeno[4,3-c]-isoxazoline in the form of colorless crystals.

¹H NMR (CDCl₃, δ in ppm): 3.73 (dd, 1H); 3.89 (s, 3H); 3.84-3.95 (m, 1H); 4.11 (dd, 1H); 4.54 (dd, 1H); 4.79 (dd, 1H); 6.61 (d, 1H); 7.81 (d, 1H).

(5-Hydroxy-1-methyl-1H-pyrazol-4-yl)-(6-methoxy-3a,4-dihydro-3H-chromeno[4,3-c]isoxazolin-9-yl)methanone (compound 2.3)

Step a)

At room temperature, 0.26 g (2.2 mmol) of thionyl chloride and a drop of dimethylformamide were added to a solution of 0.50 g (2.0 mmol) of 6-methoxy-9-hydroxycarbonyl-3a,4-dihydro-3H-chromeno[(4,3-c)]isoxazoline in 30 ml of carbon tetrachloride, and the mixture was stirred at 40-50° C. for 3 hours. The solvent was subsequently removed under reduced pressure. This gave, in quantitative yield, 6-methoxy-9-chloroformyl-3a,4-dihydro-3H-chromeno[4,3-c]isoxazoline (0.54 g) as a brownish oil.

Step b)

0.54 g (2 mmol) of 6-methoxy-9-chloroformyl-3a,4-dihydro-3H-chromeno[4,3-c]isoxazoline was dissolved in 30 ml of acetonitrile and, at 0° C., added dropwise to a solution of 0.2 g (2.0 mmol) of 1-methyl-5-hydroxypyrazole and 0.6 g (6.0 mmol) of triethylamine in 20 ml of acetonitrile. The mixture was stirred at room temperature overnight, the solvent was removed, and the residue was taken up in methylene chloride and washed with water. The solution was dried and the solvent was distilled off. The residue was dissolved in 30 ml of dioxane and admixed with 0.42 g (3.0 mmol) of potassium carbonate, and the mixture was refluxed for 7 hours. After cooling, the solvent was distilled off under reduced pressure, the residue was taken up in water and the solution was adjusted to pH=1 using 10% strength hydrochloric acid. The solution was extracted with methylene chloride, the combined organic phases were dried and the solvent was subsequently removed. This gave 0.45 g (68%) of (5-hydroxy-1-methyl-1H-pyrazol-4-yl)-(6-methoxy-3a,4-dihydro-3H-chromeno[4,3-c]isoxazolin-9-yl)methanone of m.p. 236-238° C.

¹H NMR (CDCl₃, δ in ppm): 3.66 (s, 3H); 3.84-4.2 (m, 2H); 4.02 (s, 3H); 4.12 (dd, 1H); 4.63-4.77 (m, 2H); 6.68 (d, 1H); 7.24 (s, 1H); 7.61 (d, 1H).

4. [5-Hydroxy-1-(1,1-dimethyleth-1-yl)-1H-pyrazol-4-yl]-[6-methoxy-3a,4-dihydro-3H-chromeno[4,3-c]isoxazolin-9-yl]methanone (compound 2.4)

0.54 g (2 mmol) of 6-methoxy-9-chloroformyl-3a,4-dihydro-3H-chromeno[4,3-c]-isoxazoline was dissolved in 30 ml of acetonitrile and, at 0° C., added dropwise to a solution of 0.28 g (2.0 mmol) of 1-(1,1-dimethyleth-1-yl)-5-hydroxy-1H-pyrazole and 0.6 g (6.0 mmol) of triethylamine in 20 ml of acetonitrile. The mixture was stirred at room temperature overnight, the solvent was removed, and the residue was taken up in methylene chloride and washed with water. The solution was dried, and the solvent was distilled off. The residue was dissolved in 30 ml of dioxane and admixed with 0.42 g (3.0 mmol) of potassium carbonate, and the mixture was refluxed for 7 hours. After cooling, the solvent was distilled off under reduced pressure, the residue was taken up in water and the solution was adjusted to pH=1 using 10% strength hydrochloric acid. The solution was extracted with methylene chloride, the combined organic phases were dried, and the solvent was subsequently removed. This gave 0.3 g (40%) of [5-hydroxy-1-(1,1-dimethyleth-1-yl)-1H-pyrazol-4-yl]-[6-methoxy-3a,4-dihydro-3H-chromeno[4,3-c]isoxazolin-9-yl]methanone having a melting point of 223° C.-225° C.

¹H NMR (CDCl₃, δ in ppm): 1.64 (s, 9H); 3.8-4.2 (m, 6H); 4.6-4.8 (m, 2H); 6.68 (d, 1H); 7.44 (s, 1H); 7.62 (d, 1H).

In addition to the compounds above, other tricyclic benzoylpyrazole derivatives of the formula I which were prepared or are preparable in a similar manner are listed in Tables 2 to 5: TABLE 2

physical data (m.p. [° C.]; No. X R⁴ R¹⁰ R¹¹ R¹² ¹H NMR [ppm]) 2.1 Bond SO₂CH₃ OH CH₃ H 3.03 (dd, 1H); 3.42 (s, 3H); 3.51 (s, 3H); 4.05 (m, 2H); 4.85 (t, 1H); 7.57 (s, 1H); 7.92 (d, 1H); 8.22 (d, 1H) 2.2 Bond SO₂CH₃ OCOC₆H₅ CH₃ H 3.22 (s, 3H); 3.34 (m, 2H); 3.81 (s, 3H); 3.98 (m, 2H); 4.81 (t, 1H); 7.20-8.21 (m, 8H); 2.3 O OCH₃ OH CH₃ H 236-238 2.4 O OCH₃ OH C(CH₃)₃ H 223-225 2.5 O OCH₃ OCO (3-F—C₆H₄) CH₃ H oil

TABLE 3

No. X R⁴ R¹⁰ R¹¹ R¹² physical data (m.p.[° C]) 3.1 S Cl OH CH₃ H 168-171 3.2 S Cl OH CH₂CH₃ H 115 3.3 S SCH₃ OH CH₃ H 245 3.4 S SCH₃ OH CH₂CH₃ H 222

TABLE 4

physical data (m.p. [° C.]; No. X R⁴ R¹⁰ R¹¹ R¹² ¹H NMR [ppm]) 4.1 S Cl OH CH₃ H 180° C. 4.2 S Cl OH CH₂CH₃ H 112° C.

TABLE 5

physical data (m.p. [° C.]; Nr. X R⁴ R¹⁰ R¹¹ R¹² ¹H NMR [ppm]) 5.1 O SCH₃ OH CH₃ H 201

The compounds of the formula I and their agriculturally useful salts are suitable, both in the form of isomer mixtures and in the form of the pure isomers, as herbicides. The herbicidal compositions comprising compounds of the formula I control vegetation on non-crop areas very efficiently, especially at high rates of application. They act against broad-leaved weeds and grass weeds in crops such as wheat, rice, maize, soya and cotton without causing any significant damage to the crop plants. This effect is mainly observed at low rates of application.

Depending on the application method in question, the compounds of the formula I, or herbicidal compositions comprising them, can additionally be employed in a further number of crop plants for eliminating undesirable plants. Examples of suitable crops are the following:

Allium cepa, Ananas comosus, Arachis hypogaea, Asparagus officinalis, Beta vulgaris spec. altissima, Beta vulgaris spec. rapa, Brassica napus var. napus, Brassica napus var. napobrassica, Brassica rapa var. silvestris, Camellia sinensis, Carthamus tinctorius, Carya illinoinensis, Citrus limon, Citrus sinensis, Coffea arabica (Coffea canephora, Coffea liberica), Cucumis sativus, Cynodon dactylon, Daucus carota, Elaeis guineensis, Fragaria vesca, Glycine max, Gossypium hirsutum, (Gossypium arboreum, Gossypium herbaceum, Gossypium vitifolium), Helianthus annuus, Hevea brasiliensis, Hordeum vulgare, Humulus lupulus, Ipomoea batatas, Juglans regia, Lens culinaris, Linum usitatissimum, Lycopersicon lycopersicum, Malus spec., Manihot esculenta, Medicago sativa, Musa spec., Nicotiana tabacum (N. rustica), Olea europaea, Oryza sativa, Phaseolus lunatus, Phaseolus vulgaris, Picea abies, Pinus spec., Pisum sativum, Prunus avium, Prunus persica, Pyrus communis, Ribes sylvestre, Ricinus communis, Saccharum officinarum, Secale cereale, Solanum tuberosum, Sorghum bicolor (s. vulgare), Theobroma cacao, Trifolium pratense, Triticum aestivum, Triticum durum, Vicia faba, Vitis vinifera and Zea mays.

In addition, the compounds of the formula I may also be used in crops which tolerate the action of herbicides owing to breeding, including genetic engineering methods.

The compounds of the formula I, or the herbicidal compositions comprising them, can be used for example in the form of ready-to-spray aqueous solutions, powders, suspensions, also highly-concentrated aqueous, oily or other suspensions or dispersions, emulsions, oil dispersions, pastes, dusts, materials for broadcasting, or granules, by means of spraying, atomizing, dusting, spreading or watering. The use forms depend on the intended purpose; in any case, they should guarantee the finest possible distribution of the active compounds according to the invention.

The herbicidal compositions comprise a herbicidally effective amount of at least one compound of the formula I or an agriculturally useful salt of I and auxiliaries which are customarily used for formulating crop protection agents.

Suitable for use as inert auxiliaries are essentially the following:

mineral oil fractions of medium to high boiling point, such as kerosene and diesel oil, furthermore coal-tar oils and oils of vegetable or animal origin, aliphatic, cyclic and aromatic hydrocarbons, for example paraffin, tetrahydronaphthalene, alkylated naphthalenes and their derivatives, alkylated benzenes or their derivatives, alcohols such as methanol, ethanol, propanol, butanol and cyclohexanol, ketones such as cyclohexanone, strongly polar solvents, for example amines such as N-methylpyrrolidone, and water.

Aqueous use forms can be prepared from emulsion concentrates, suspensions, pastes, wettable powders or water-dispersible granules by adding water. To prepare emulsions, pastes or oil dispersions, the tricyclic benzoylpyrazole derivatives of the formula I, either as such or dissolved in an oil or solvent, can be homogenized in water by means of a wetting agent, tackifier, dispersant or emulsifier. Alternatively, it is possible to prepare concentrates comprising active compound, wetting agent, tackifier, dispersant or emulsifier and, if desired, solvent or oil, which are suitable for dilution with water.

Suitable surfactants are the alkali metal salts, alkaline earth metal salts and ammonium salts of aromatic sulfonic acids, e.g. ligno-, phenol-, naphthalene- and dibutylnaphthalenesulfonic acid, and of fatty acids, alkyl- and alkylarylsulfonates, alkyl sulfates, lauryl ether sulfates and fatty alcohol sulfates, and salts of sulfated hexa-, hepta- and octadecanols, and also of fatty alcohol glycol ethers, condensates of sulfonated naphthalene and its derivatives with formaldehyde, condensates of naphthalene or of the naphthalenesulfonic acids with phenol and formaldehyde, polyoxyethylene octylphenol ether, ethoxylated isooctyl-, octyl- or nonylphenol, alkylphenyl or tributylphenyl polyglycol ether, alkylaryl polyether alcohols, isotridecyl alcohol, fatty alcohol/ethylene oxide condensates, ethoxylated castor oil, polyoxyethylene alkyl ethers or polyoxypropylene alkyl ethers, lauryl alcohol polyglycol ether acetate, sorbitol esters, lignin-sulfite waste liquors or methylcellulose.

Powders, materials for broadcasting and dusts can be prepared by mixing or grinding the active compounds together with a solid carrier.

Granules, e.g. coated granules, impregnated granules and homogeneous granules, can be prepared by binding the active compounds to solid carriers. Solid carriers are mineral earths such as silicas, silica gels, silicates, talc, kaolin, limestone, lime, chalk, bole, loess, clay, dolomite, diatomaceous earth, calcium sulfate, magnesium sulfate and magnesium oxide, ground synthetic materials, fertilizers such as ammonium sulfate, ammonium phosphate, ammonium nitrate and ureas, and products of vegetable origin, such as cereal meal, tree bark meal, wood meal and nutshell meal, cellulose powders, or other solid carriers.

The concentrations of the compounds of the formula I in the ready-to-use preparations can be varied within wide ranges. In general, the formulations comprise approximately from 0.001 to 98% by weight, preferably 0.01 to 95% by weight, of at least one active compound. The active compounds are employed in a purity of from 90% to 100%, preferably 95% to 100% (according to NMR spectrum).

The following formulation examples illustrate the preparation of such formulations:

-   I. 20 parts by weight of the compound No. 2.2 are dissolved in a     mixture composed of 80 parts by weight of alkylated benzene, parts     by weight of the adduct of from 8 to 10 mol of ethylene oxide to 1     mol of oleic acid N-monoethanolamide, 5 parts by weight of calcium     salt of dodecylbenzenesulfonic acid and 5 parts by weight of the     adduct of 40 mol of ethylene oxide to 1 mol of castor oil. Pouring     the solution into 100,000 parts by weight of water and finely     distributing it therein gives an aqueous dispersion which comprises     0.02% by weight of the active compound. -   II. 20 parts by weight of the compound No. 3.1 are dissolved in a     mixture composed of 40 parts by weight of cyclohexanone, 30 parts by     weight of isobutanol, 20 parts by weight of the adduct of 7 mol of     ethylene oxide to 1 mol of isooctylphenol and 10 parts by weight of     the adduct of 40 mol of ethylene oxide to 1 mol of castor oil.     Pouring the solution into 100,000 parts by weight of water and     finely distributing it therein gives an aqueous dispersion which     comprises 0.02% by weight of the active compound. -   III. 20 parts by weight of the compound No. 2.3 are dissolved in a     mixture composed of 25 parts by weight of cyclohexanone, 65 parts by     weight of a mineral oil fraction of boiling point 210 to 280° C. and     10 parts by weight of the adduct of 40 mol of ethylene oxide to 1     mol of castor oil. Pouring the solution into 100,000 parts by weight     of water and finely distributing it therein gives an aqueous     dispersion which comprises 0.02% by weight of the active compound. -   IV. 20 parts by weight of the compound No. 2.4 are mixed thoroughly     with 3 parts by weight of the sodium salt of     diisobutylnaphthalenesulfonic acid, 17 parts by weight of the sodium     salt of a lignosulfonic acid from a sulfite waste liquor and 60     parts by weight of pulverulent silica gel, and the mixture is ground     in a hammer mill. Finely distributing the mixture in 20,000 parts by     weight of water gives a spray mixture which comprises 0.1% by weight     of the active compound. -   V. 3 parts by weight of the compound No. 2.3 are mixed with 97 parts     by weight of finely divided kaolin. This gives a dust which     comprises 3% by weight of the active compound. -   VI. 20 parts by weight of the compound No. 2.4 are mixed intimately     with 2 parts by weight of calcium salt of dodecylbenzenesulfonic     acid, 8 parts by weight of fatty alcohol polyglycol ether, 2 parts     by weight of sodium salt of a phenol/urea/formaldehyde condensate     and 68 parts by weight of a paraffinic mineral oil. This gives a     stable oily dispersion. -   VII. 1 part by weight of the compound No. 2.2 is dissolved in a     mixture composed of 70 parts by weight of cyclohexanone, 20 parts by     weight of ethoxylated isooctylphenol and 10 parts by weight of     ethoxylated castor oil. This gives a stable emulsion concentrate. -   VIII. 1 part by weight of the compound No. 3.1 is dissolved in a     mixture composed of 80 parts by weight of cyclohexanone and 20 parts     by weight of Wettol® EM 31 (=nonionic emulsifier based on     ethoxylated castor oil). This gives a stable emulsion concentrate.

The compounds of the formula I or the herbicidal compositions can be applied pre- or post-emergence. If the active compounds are less well tolerated by certain crop plants, application techniques may be used in which the herbicidal compositions are sprayed, with the aid of the spraying equipment, in such a way that as far as possible they do not come into contact with the leaves of the sensitive crop plants, while the active compounds reach the leaves of undesirable plants growing underneath, or the bare soil surface (post-directed, lay-by).

The rates of application of the compound of the formula I are from 0.001 to 3.0, preferably 0.01 to 1.0, kg/ha of active substance (a.s.), depending on the control target, the season, the target plants and the growth stage.

To widen the spectrum of action and to achieve synergistic effects, the tricyclic benzylpyrazole derivatives of the formula I may be mixed with a large number of representatives of other herbicidal or growth-regulating active compound groups and applied concomitantly. Suitable components for mixtures are, for example, 1,2,4-thiadiazoles, 1,3,4-thiadiazoles, amides, aminophosphoric acid and its derivatives, aminotriazoles, anilides, aryloxy-/heteroaryloxyalkanoic acids and their derivatives, benzoic acid and its derivatives, benzothiadiazinones, 2-aroyl-1,3-cyclohexanediones, heteroaryl aryl ketones, benzylisoxazolidinones, meta-CF₃-phenyl derivatives, carbamates, quinoline carboxylic acid and its derivatives, chloroacetanilides, cyclohexenone oxime ether derivatives, diazines, dichloropropionic acid and its derivatives, dihydrobenzofurans, dihydrofuran-3-ones, dinitroanilines, dinitrophenols, diphenyl ethers, dipyridyls, halocarboxylic acids and their derivatives, ureas, 3-phenyluracils, imidazoles, imidazolinones, N-phenyl-3,4,5,6-tetrahydrophthalimides, oxadiazoles, oxiranes, phenols, aryloxy- and hetaryloxyphenoxypropionic esters, phenylactic acid and its derivatives, 2-phenylpropionic acid and its derivatives, pyrazoles, phenylpyrazoles, pyridazines, pyridinecarboxylic acid and its derivatives, pyrimidyl ethers, sulfonamides, sulfonylureas, triazines, triazinones, triazolinones, triazolecarboxamides and uracils.

It may furthermore be advantageous to apply the compounds of the formula I, alone or in combination with other herbicides, in the form of a mixture with other crop protection agents, for example together with agents for controlling pests or phytopathogenic fungi or bacteria. Also of interest is the miscibility with mineral salt solutions, which are employed for treating nutritional and trace element deficiencies. Non-phytotoxic oils and oil concentrates may also be added.

USE EXAMPLES

The herbicidal activity of the tricyclic benzylpyrazole derivatives of the formula I was demonstrated by the following greenhouse experiments:

The culture containers used were plastic pots containing loamy sand with approximately 3.0% of humus as the substrate. The seeds of the test plants were sown separately for each species.

For the pre-emergence treatment, the active compounds, which had been suspended or emulsified in water, were applied directly after sowing by means of finely distributing nozzles. The containers were irrigated gently to promote germination and growth and subsequently covered with transparent plastic hoods until the plants had rooted. This cover causes uniform germination of the test plants, unless this was adversely affected by the active compounds.

For post-emergence treatment, the test plants were first grown to a plant height of from 3 to 15 cm, depending on the plant habit, and only then treated with the active compounds which had been suspended or emulsified in water. For this purpose, the test plants were either sown directly and grown in the same containers, or they were first grown separately as seedlings and transplanted into the test containers a few days prior to the treatment. The application rate for the post-emergence treatment was 0.5 or 0.25 kg of a.s./ha.

Depending on the species, the plants were kept at 10-25° C. or 20-35° C. The test period extended over 2 to 4 weeks. During this time, the plants were tended, and their response to the individual treatments was evaluated.

Evaluation was carried out using a scale from 0 to 100. 100 means no emergence of the plants, or complete destruction of at least the above-ground parts, and 0 means no damage, or normal course of growth.

The plants used in the greenhouse trials were of the following species: Scientific Name Common Name Chenopodium album lambsquarters (goosefoot) Echinochloa crusgalli barnyardgrass Setaria viridis green foxtail Solanum nigrum black nightshade Veronica ssp. speadwell

At application rates of 0.5 or 0.25 kg/ha, the compound 2.2 shows very good activity against the abovementioned undesired broad-leaved weeds and weed grasses when applied by the post-emergence method. 

1.-20. (canceled)
 21. A tricyclic benzoylpyrazole compound of formula I

where: X is oxygen, sulfur, S═O, S(═O)₂, CR⁶R⁷, or NR⁸; Y together with the two carbons to which it is attached forms a saturated, partially saturated or unsaturated 5- or 6-membered heterocycle which contains one to three identical or different heteroatoms selected from the following group: oxygen, sulfur and nitrogen; R¹, R², R⁶, R⁷ are hydrogen, C₁-C₆-alkyl, C₁-C₆-haloalkyl, C₁-C₆-alkoxy or C₁-C₆-haloalkoxy; R³ is halogen, C₁-C₆-alkyl, C₁-C₆-haloalkyl, C₁-C₆-alkoxy or C₁-C₆-haloalkoxy; R⁴ is hydrogen, nitro, halogen, cyano, C₁-C₆-alkyl, C₁-C₆-haloalkyl, C₁-C₆-alkoxy, C₁-C₆-haloalkoxy, C₁-C₆-alkylthio, C₁-C₆-haloalkylthio, C₁-C₆-alkylsulfinyl, C₁-C₆-haloalkylsulfinyl, C₁-C₆-alkylsulfonyl, C₁-C₆-haloalkylsulfonyl, aminosulfonyl, N—(C₁-C₆-alkyl)aminosulfonyl, N,N-di(C₁-C₆-alkyl)aminosulfonyl, N—(C₁-C₆-alkylsulfonyl)amino, N—(C₁-C₆-haloalkylsulfonyl)amino, N—(C₁-C₆-alkyl)-N—(C₁-C₆-alkylsulfonyl)amino or N—(C₁-C₆-alkyl)-N—(C₁-C₆-haloalkylsulfonyl)amino; R⁵ is hydrogen, C₁-C₆-alkyl or halogen; R⁸ is hydrogen, C₁-C₆-alkyl, C₁-C₆-haloalkyl, C₁-C₆-alkylcarbonyl, formyl, C₁-C₆-alkoxycarbonyl, C₁-C₆-haloalkoxycarbonyl, C₁-C₆-alkylsulfonyl or C₁-C₆-haloalkylsulfonyl; l is 0, 1 or 2; R⁹ is a radical IIa or IIb

where R¹⁰ is hydroxyl, mercapto, halogen, OR¹³, SR¹³, SO₂R¹⁴, NR¹⁵R¹⁶ or N-bonded heterocyclyl, where the heterocyclyl radical may be partially or fully halogenated and/or may carry one to three of the following radicals: nitro, cyano, C₁-C₄-alkyl, C₁-C₄-haloalkyl, C₁-C₄-alkoxy or C₁-C₄-haloalkoxy; R¹¹ is hydrogen, C₁-C₆-alkyl, C₁-C₆-haloalkyl, C₃-C₆-cycloalkyl, hydroxyl, C₁-C₆-alkoxy or C₁-C₆-haloalkoxy; R¹² is hydrogen, halogen, C₁-C₆-alkyl, C₁-C₆-haloalkyl, hydroxyl, C₁-C₆-alkoxy, C₁-C₆-haloalkoxy, C₁-C₆-alkylthio or C₁-C₆-haloalkylthio; R¹³ is C₁-C₆-alkyl, C₃-C₆-alkenyl, C₃-C₆-haloalkenyl, C₃-C₆-alkynyl, C₃-C₆-haloalkynyl, C₃-C₆-cycloalkyl, C₁-C₂₀-alkylcarbonyl, C₂-C₂₀-alkenylcarbonyl, C₂-C₆-alkynylcarbonyl, C₃-C₆-cycloalkylcarbonyl, C₁-C₆-alkoxycarbonyl, C₃-C₆-alkenyloxycarbonyl, C₃-C₆-alkynyloxycarbonyl, C₁-C₆-alkylthiocarbonyl, C₁-C₆-alkylaminocarbonyl, C₃-C₆-alkenylaminocarbonyl, C₃-C₆-alkynylaminocarbonyl, N,N-di(C₁-C₆-alkyl)aminocarbonyl, N—(C₃-C₆-alkenyl)-N—(C₁-C₆-alkyl)aminocarbonyl, N—(C₃-C₆-alkynyl)-N—(C₁-C₆-alkyl)aminocarbonyl, N—(C₁-C₆-alkoxy)-N—(C₁-C₆-alkyl)aminocarbonyl, N—(C₃-C₆-alkenyl)-N—(C₁-C₆-alkoxy)aminocarbonyl, N—(C₃-C₆-alkynyl)-N—(C₁-C₆-alkoxy)aminocarbonyl, di(C₁-C₆-alkyl)aminothiocarbonyl, C₁-C₆-alkylcarbonyl-C₁-C₆-alkyl, C₁-C₆-alkoxyimino-C₁-C₆-alkyl, N—(C₁-C₆-alkylamino)imino-C₁-C₆-alkyl or N,N-di(C₁-C₆-alkylamino)imino-C₁-C₆-alkyl, where the abovementioned alkyl, cycloalkyl and alkoxy radicals may be partially or fully halogenated and/or may carry one to three of the following groups: cyano, C₁-C₄-alkoxy, C₁-C₄-alkylthio, di(C₁-C₄-alkyl)amino, C₁-C₄-alkylcarbonyl, C₁-C₄-alkoxycarbonyl, C₁-C₄-alkoxy-C₁-C₄-alkoxycarbonyl, di(C₁-C₄-alkyl)amino-C₁-C₄-alkoxycarbonyl, hydroxycarbonyl, C₁-C₄-alkylaminocarbonyl, di(C₁-C₄-alkyl)aminocarbonyl, aminocarbonyl, C₁-C₄-alkylcarbonyloxy or C₃-C₆-cycloalkyl; is phenyl, heterocyclyl, phenyl-C₁-C₆-alkyl, heterocyclyl-C₁-C₆-alkyl, phenylcarbonyl-C₁-C₆-alkyl, heterocyclylcarbonyl-C₁-C₆-alkyl, phenylcarbonyl, heterocyclylcarbonyl, phenoxycarbonyl, phenyloxythiocarbonyl, heterocyclyloxycarbonyl, heterocyclyloxythiocarbonyl, phenylaminocarbonyl, N—(C₁-C₆-alkyl)-N-(phenyl)aminocarbonyl, heterocyclylaminocarbonyl, N—(C₁-C₆-alkyl)-N-(heterocyclyl)aminocarbonyl, phenyl-C₂-C₆-alkenylcarbonyl or heterocyclyl-C₂-C₆-alkenylcarbonyl, where the phenyl and the heterocyclyl radical of the 18 lastmentioned substitutents may be partially or fully halogenated and/or may carry one to three of the following radicals: nitro, cyano, C₁-C₄-alkyl, C₁-C₄-haloalkyl, C₁-C₄-alkoxy, C₁-C₄-haloalkoxy, heterocyclyl or N-bonded heterocyclyl, where the two lastmentioned substitutents for their part may be partially or fully halogenated and/or may carry one to three of the following radicals: nitro, cyano, C₁-C₄-alkyl, C₁-C₄-haloalkyl, C₁-C₄-alkoxy or C₁-C₄-haloalkoxy; R¹⁴ is C₁-C₆-alkyl, C₃-C₆-alkenyl, C₃-C₆-haloalkenyl, C₃-C₆-alkynyl, C₃-C₆-haloalkynyl, C₃-C₆-cycloalkyl, C₁-C₆-alkoxy, di(C₁-C₆-alkyl)amino or di(C₁-C₆-haloalkyl)amino, where the abovementioned alkyl, cycloalkyl and alkoxy radicals may be partially or fully halogenated and/or may carry one to three of the following groups: cyano, C₁-C₄-alkoxy, C₁-C₄-alkylthio, di(C₁-C₄-alkyl)amino, C₁-C₄-alkylcarbonyl, C₁-C₄-alkoxycarbonyl, C₁-C₄-alkoxy-C₁-C₄-alkoxycarbonyl, di(C₁-C₄-alkyl)amino-C₁-C₄-alkoxycarbonyl, hydroxycarbonyl, C₁-C₄-alkylaminocarbonyl, di(C₁-C₄-alkyl)aminocarbonyl, aminocarbonyl, C₁-C₄-alkylcarbonyloxy or C₃-C₆-cycloalkyl; is phenyl, heterocyclyl, phenyl-C₁-C₆-alkyl, heterocyclyl-C₁-C₆-alkyl, phenoxy, heterocyclyloxy, where the phenyl and the heterocyclyl radical of the lastmentioned substitutents may be partially or fully halogenated and/or may carry one to three of the following radicals: nitro, cyano, C₁-C₄-alkyl, C₁-C₄-haloalkyl, C₁-C₄-alkoxy or C₁-C₄-haloalkoxy; R¹⁵ is C₁-C₆-alkyl, C₃-C₆-alkenyl, C₃-C₆-haloalkenyl, C₃-C₆-alkynyl, C₃-C₆-haloalkynyl, C₃-C₆-cycloalkyl, C₁-C₆-alkoxy, C₃-C₆-alkenyloxy, C₃-C₆-alkynyloxy, di(C₁-C₆-alkyl)amino or C₁-C₆-alkylcarbonylamino, where the abovementioned alkyl, cycloalkyl and alkoxy radicals may be partially or fully halogenated and/or may carry one to three radicals of the following group: cyano, C₁-C₄-alkoxy, C₁-C₄-alkylthio, di(C₁-C₄-alkyl)amino, C₁-C₄-alkylcarbonyl, C₁-C₄-alkoxycarbonyl, C₁-C₄-alkoxy-C₁-C₄-alkoxycarbonyl, di(C₁-C₄-alkyl)amino-C₁-C₄-alkoxycarbonyl, hydroxycarbonyl, C₁-C₄-alkylaminocarbonyl, di(C₁-C₄-alkyl)aminocarbonyl, aminocarbonyl, C₁-C₄-alkylcarbonyloxy or C₃-C₆-cycloalkyl; is phenyl, heterocyclyl, phenyl-C₁-C₆-alkyl or heterocyclyl-C₁-C₆-alkyl, where the phenyl or heterocyclyl radical of the four lastmentioned substitutents may be partially or fully halogenated and/or may carry one to three of the following radicals: nitro, cyano, C₁-C₄-alkyl, C₁-C₄-haloalkyl, C₁-C₄-alkoxy or C₁-C₄-haloalkoxy; R¹⁶ is C₁-C₆-alkyl, C₃-C₆-alkenyl, C₃-C₆-alkynyl or C₁-C₆-alkylcarbonyl; or an agriculturally useful salt thereof.
 22. The tricyclic benzoylpyrazole compound of formula I defined in claim 21 where R⁹ is IIa.
 23. The tricyclic benzoylpyrazole compound of formula I defined in claim 21 where X is oxygen, sulfur or CR⁶R⁷.
 24. The tricyclic benzoylpyrazole compound of formula I defined in claim 21 where Y together with the two carbons to which it is attached forms a heterocycle selected from the following group: dihydroisoxazolediyl, isoxazolediyl or tetrahydroisoxazolediyl.
 25. The tricyclic benzoylpyrazole compound of formula I defined in claim 21 where R¹, R² are hydrogen; R³ is C₁-C₆-alkyl; R⁴ is nitro, halogen, C₁-C₆-alkyl, C₁-C₆-haloalkyl, C₁-C₆-alkoxy, C₁-C₆-alkylthio or C₁-C₆-alkylsulfonyl; R⁵ is hydrogen; l is 0 oder
 1. 26. The tricyclic benzoylpyrazole compound of formula I defined in claim 21 where R¹⁰ is hydroxyl; R¹¹ is C₁-C₆-alkyl or C₃-C₆-cycloalkyl; R¹² is hydrogen or C₁-C₆-alkyl.
 27. A process for preparing the compound of formula I where R¹⁰=halogen as claimed in claim 21, which comprises reacting a tricyclic benzoylpyrazole compound of formula Iα (=I where R¹⁰=hydroxyl),

where the variables R¹ to R⁵, R¹¹ and R¹², X, Y and l are as defined in claim 21, with a halogenating agent.
 28. A process for preparing the compound of formula I where R¹⁰=OR¹³ as claimed in claim 21, which comprises reacting a tricyclic benzoylpyrazole compound of formula Iα (=I where R¹⁰=hydroxyl),

where the variables R¹ to R⁵, R¹¹ and R¹², X, Y and l are as defined in claim 21, with a compound of formula III L¹R¹³  III where the variable R¹³ is as defined in claim 21 and L¹ is a nucleophilically replaceable leaving group.
 29. A process for preparing the compound of formula I where R¹⁰=OR¹³, SR¹³, NR¹⁵R¹⁶ or N-bonded heterocyclyl as claimed in claim 21, which comprises reacting a compound of formula Iβ (≡I where R¹⁰=halogen),

where the variables R¹ to R⁵, R¹¹ and R¹², X, Y and l are as defined in claim 21, with a compound of formula IVα, IVβ, IVγ or IVδ

HOR¹³HSR¹³NHR¹⁵R¹⁶H(N-bonded heterocyclyl) Ivo. IVp ivy IV8 where the variables R¹³ to R¹⁶ are as defined in claim 21, optionally in the presence of a base.
 30. A process for preparing the compound of formula I where R¹⁰=SO₂R¹⁴ as claimed in claim 21, which comprises reacting a compound of formula Iγ (≡I where R¹⁰=SR¹⁴),

where the variables R¹ to R⁵, R¹¹ and R¹², X, Y and l are as defined in claim 21, with an oxidizing agent.
 31. A process for preparing the compound of formula I where R⁹=IIa as claimed in claim 21, which comprises reacting a metalated pyrazole compound of formula V where M is a metal and R¹⁰ to R¹² are as defined in claim 21, except for R¹⁰=hydroxyl and mercapto, with a tricyclic benzoic acid compound of formula VIα where R¹ to R⁵, X, Y and l are as defined in claim 21 and L² is a nucleophilically replaceable leaving group.


32. A process for preparing the compound of formula Iα (=I where R¹⁰=hydroxyl) as claimed in claim 21, which comprises acylating a pyrazole of formula VII in which the variables R¹¹ and R¹² are as defined in claim 21

with an activated tricyclic benzoic acid of formula VIβ or with a tricyclic benzoic acid of formula VIγ,

where the variables R¹ to R⁵, X, Y and l are as defined in claim 21 and L³ is a nucleophilically replaceable leaving group, and rearranging the acylation product, optionally in the presence of a catalyst.
 33. A process for preparing the compound of formula Iα (≡I where R¹⁰=hydroxyl) as claimed in claim 21, which comprises reacting a pyrazole of formula VII in which the variables R¹¹ and R¹² are as defined in claim 21, or an alkali metal salt thereof,

with a tricyclic benzene compound of formula IX where L⁴ is a leaving group and the variables X, Y, R¹ to R⁵ and l are as defined in claim 21

in the presence of carbon monoxide, a catalyst and a base.
 34. A composition, comprising a herbicidally effective amount of at least one compound of formula I or an agriculturally useful salt thereof as claimed in claim 21 and auxiliaries which are customary for formulating crop protection agents.
 35. A process for preparing the composition defined in claim 34, which comprises mixing a herbicidally effective amount of at least one compound of formula I or an agriculturally useful salt thereof and auxiliaries which are customary for formulating crop protection agents.
 36. A method for controlling undesirable vegetation, which comprises allowing a herbicidally effective amount of at least one compound of formula I or an agriculturally useful salt thereof as claimed in claim 21 to act on plants, their habitat or on seed.
 37. A tricyclic benzoic acid compound of formula VI

in which the variables X, Y, R¹ to R³ and R⁵ and l are as defined in claim 21 and R⁴ is nitro, halogen, cyano, C₁-C₆-alkyl, C₁-C₆-haloalkyl, C₁-C₆-alkoxy, C₁-C₆-haloalkoxy, C₁-C₆-alkylthio, C₁-C₆-haloalkylthio, C₁-C₆-alkylsulfinyl, C₁-C₆-haloalkylsulfinyl, C₁-C₆-alkylsulfonyl, C₁-C₆-haloalkylsulfonyl, aminosulfonyl, N—(C₁-C₆-alkyl)aminosulfonyl, N,N-di(C₁-C₆-alkyl)aminosulfonyl, N—(C₁-C₆-alkylsulfonyl)amino, N—(C₁-C₆-haloalkylsulfonyl)amino, N—(C₁-C₆-alkyl)-N—(C₁-C₆-alkylsulfonyl)amino or N—(C₁-C₆-alkyl)-N—(C₁-C₆-haloalkylsulfonyl)amino; R¹⁷ is hydroxyl or a radical which can be removed by hydrolysis.
 38. A tricyclic benzene compound of formula IX

in which the variables X, Y, R¹ to R³ and R⁵ and l are as defined in claim 21 and R⁴ is nitro, halogen, cyano, C₁-C₆-alkyl, C₁-C₆-haloalkyl, C₁-C₆-alkylthio, C₁-C₆-haloalkylthio, C₁-C₆-alkylsulfinyl, C₁-C₆-haloalkylsulfinyl, C₁-C₆-alkylsulfonyl, C₁-C₆-haloalkylsulfonyl, aminosulfonyl, N—(C₁-C₆-alkyl)aminosulfonyl, N,N-di(C₁-C₆-alkyl)aminosulfonyl, N—(C₁-C₆-alkylsulfonyl)amino, N—(C₁-C₆-haloalkylsulfonyl)amino, N—(C₁-C₆-alkyl)-N—(C₁-C₆-alkylsulfonyl)amino or N—(C₁-C₆-alkyl)-N—(C₁-C₆-haloalkylsulfonyl)amino; R⁵ is hydrogen or C₁-C₆-alkyl; L⁴ is halogen, C₁-C₆-alkylsulfonyloxy, C₁-C₆-haloalkylsulfonyloxy or phenylsulfonyloxy, where the phenyl ring of the lastmentioned radical may be unsubstituted or partially or fully halogenated and/or may carry one to three of the following radicals: nitro, cyano, C₁-C₄-alkyl, C₁-C₄-haloalkyl, C₁-C₄-alkoxy or C₁-C₄-haloalkoxy.
 39. An aniline compound of formula XV

in which the variables X, Y, R¹ to R³ and R⁵ and 1 are in each case as defined in claim 21 and R⁴ is nitro, halogen, cyano, C₁-C₆-haloalkyl, C₁-C₆-alkoxy, C₁-C₆-haloalkoxy, C₁-C₆-alkylthio, C₁-C₆-haloalkylthio, C₁-C₆-alkylsulfinyl, C₁-C₆-haloalkylsulfinyl, C₁-C₆-alkylsulfonyl, C₁-C₆-haloalkylsulfonyl, aminosulfonyl, N—(C₁-C₆-alkyl)aminosulfonyl, N,N-di(C₁-C₆-alkyl)aminosulfonyl, N—(C₁-C₆-alkylsulfonyl)amino, N—(C₁-C₆-haloalkylsulfonyl)amino, N—(C₁-C₆-alkyl)-N—(C₁-C₆-alkylsulfonyl)amino or N—(C₁-C₆-alkyl)-N—(C₁-C₆-haloalkylsulfonyl)amino.
 40. A nitrile compound of formula XVI

in which the variables X, Y, R¹ to R³ and l are in each case as defined in claim 21 and R⁴ is nitro, halogen, cyano, C₁-C₆-haloalkyl, C₁-C₆-alkylthio, C₁-C₆-haloalkylthio, C₁-C₆-alkylsulfinyl, C₁-C₆-haloalkinylsulfinyl, C₁-C₆-alkylsulfonyl, C₁-C₆-haloalkylsulfonyl, aminosulfonyl, N—(C₁-C₆-alkyl)aminosulfonyl, N,N-di-(C₁-C₆-alkyl)aminosulfonyl, N—(C₁-C₆-alkylsulfonyl)amino, N—(C₁-C₆-haloalkylsulfonyl)amino, N—(C₁-C₆-alkyl)-N—(C₁-C₆-alkylsulfonyl)amino or N—(C₁-C₆-alkyl)-N—(C₁-C₆-haloalkylsulfonyl)amino; R⁵ is hydrogen or C₁-C₆-alkyl.
 41. The compound of formula I defined in claim 21, wherein X is O or S; Y together with the two carbons to which it is attached forms an isoxazole ring which is saturated, partially saturated or unsaturated; and R⁹ is a radical IIa.
 42. The compound of formula I defined in claim 41, wherein R¹⁰ is hydroxyl, mercapto, halogen, OR¹³, SR¹³, SO₂R¹⁴ or NR¹⁵R¹⁶. 